GB2520098A

GB2520098A - Insecticidal compounds

Info

Publication number: GB2520098A
Application number: GB1410899.7A
Authority: GB
Inventors: Thomas Pitterna; Christopher Richard Ayles Godfrey; Ottmar Franz Hueter; Andre Denis Stoller; Pierre Joseph Marcel Jung; Andrew Edmunds
Original assignee: Syngenta Participations AG
Current assignee: Syngenta Participations AG
Priority date: 2013-07-03
Filing date: 2014-06-19
Publication date: 2015-05-13
Also published as: GB201410899D0; GB2520098A8

Abstract

The present invention relates to bis-amide derivatives of formula (I): wherein Q1 is a saturated 4-6-membered heterocyclic ring comprising 1-2 sulfur atoms in addition to the carbon atoms, preferably a thietan-3-yl, dithiolan-4-yl or tetrahydrothiopyran-4-yl group, which may be unsubstituted or substituted on a sulphur atom with one or more substituents selected from =O, =N-Z and =NCZ1Z2; Z is H or cyano; Z1 and Z2 are cyano or together form a C(O)-O-CH2-C(O)- or C(O)-S-CH2-C(O)- bridge; Y1 and Y5 are Cl, Br, I, C1-4alkyl, C1-4alkoxy, C1-4haloalkyl, C1-4haloalkoxy, C1-4alkylthio, C1-4alkylsulfinyl, C1-4alkylsulfonyl or C1-4alkoxy- C1-4alkyl; Y3 is C1-4haloalkyl; Xa is H, methoxy or halogen; Xb is H, halogen or cyano; R1 and R2 are H or substituents; or an agronomically acceptable salt thereof may be useful as an insecticide, in particular insecticidal, acaricidal, nematicidal or molluscicidal activity. Methods of preparing these compounds, including intermediates, and insecticidal, acaricidal, nematicidal or molluscicidal compositions comprising them are also disclosed.

Description

Intellectual Property Office Application No. GB1410899.7 RTTVI Date:23 March 2015 The following terms are registered trade marks and should be read as such wherever they occur in this document: Phenornenex (page 149) Intellectual Property Office is an operating name of the Patent Office www.gov.uk/ipo

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INSECTICIDAL COMPOUNDS

The present invention relates to bis-amide derivatives, to processes and intermediates for preparing them, to methods of using them to control insect, acarine, nematode and mollusc pests, and to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising them.

Compounds having insecticidal properties are disclosed in EP1714958, JP200630677], WO2006]37376, EPl9l6236, W020070]7075, W02008000438, ID W02008/074427, W02009049845 and WO2OIOI 27928. There exists a need for alternative methods of control of pests. PreferaNy, new compounds may possess improved insecticidal properties, such as improved efficacy, improved selectivity, reduced toxicity, lower tendency to generate resistance or activity against a broader range of pests. Compounds may be more advantageously formulated or provide more efficient delivery and retention at sites of action, IS or may be more readily biodegradable.

It has surprisingly been found that certain bisamide derivatives, which are substituted by an arylpertluoroalkyl group and a saturated heterocyclic ring containing sulfur, have beneficial properties, which makes them particularly suitable for use as insecticides.

The present invention therefore provides a compound of formula (I)

RL

Xt_,, (I) R2 N2 wherein Q1 is a saturated 4-to 6-membered heterocyclic ring comprising one or two sulftir atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from =0, =N-Z or CZ1Z2; Z is hydrogen or cyano Z' is cyano Z2 is cyano or Z' and Z2, taken together, fonn a bridge -C(O)-O-CH2-C(O)-or -C(O)-S-CH2-C(O)-Q2 is a moiety of formula (II) Yl (II) y5y3 wherein Y1 is selected from Cl, Br, I, Ci.4alkyl, Ci.4alkoxy, Ci.4haloalkyl, Ci.4haloalkoxy, Ci 4alkylthio, C1.4alkylsulfinyl, C i4alkylsulfonyl or Ci4alkoxy-C1.4alkyl Y' is selected from Cl, Br, 1, Ci 4alkyl, Ci 4alkoxy, Ci.4haloalkyl, Ci.4haloalkoxy, Ci 4alkylthio, Ci.4alkylsulfinyl, C i4alkylsulfonyl or Ci4alkoxy-Ci.4alkyl Y3 is Ci.4haloalkyl X' is hydrogen, methoxy or halogen Xb is hydrogen, halogen or cyano R' is selected from hydrogen, C1 -Cgalkyl, C2-Csalkenyl, C2-Cgalkynyl, Ci -Cgalkykarbonyl, C i-Csalkoxycarbonyl, hydroxyl, C i-Cgalkyloxy, and aminocarbonyl-C i-C4alkylene; 1(2 is selected from hydrogen, Ci-Cgalkyl, C2-C8alkenyl, C2-Cgalkynyl, Ci-Cgalkylcarbonyl, C -Csallcoxycarbonyl, hydroxyl, C -Csalky!oxy, and aminocarbonyl-C i-C4allcylene; and 1 and G2 are both oxygen; or an agrochemically acceptable salt thereof.

The compounds of formula (I) may exist in different geomeffic or optical isomers (enantiomers and/or diasteroisomers) or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds.

Each alkyl moiety either alone or as part of a larger group (such as alkoxy, alkoxy-carbonyl, alkylcarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl) is a straight or branched chain and is, for example, methyl, ethyl, n-propy, n-butyl, iso-propyl, n-butyl, sec-butyl, iso-butyl or tert-butvl. The alkyl groups are preferably C1 to C alkyl groups, more preferably C1-C4 and most preferably C1-C3 alkyl groups.

In a preferred embodiment the present invention provides a compound of formula (I)

RLN

Xt% (I) R2 N,2 wherein Q' is a saturated 4-to 6-membered heterocyclic ring comprising one or two sulfur atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from 0, =N-Z or CZ'Z2; Z is hydrogen or cyano Z' is cyano Z2 is cyano or Z' and Z2, taken together, form a bridge -C(0)-0-Cl-12-C(O)-or -C(0)-S-Cl-12-C(O)-Q2 is a moiety of formula (II) Yl (II) Y5Y3 wherein Y1 is selected from Cl, Br, I, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, trifluoromethylsuffinyl, trifluoromethylsulfonyl or methoxymethyl Y5 is selected from Cl, Br, I, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl or methoxymethyl Y3 is heptafluoroprop-2-yl or nonafluorobut-2-yl xa is hydrogen, methoxy or halogen Xb is hydrogen, halogen or cyano R1 is selected from hydrogen, C i-Csalkyl, C2-Csalkenyl, C2-Csalkynyl, C1-C8alkytharbonyl, C i-Csalkoxycarbonyl, hydroxyl, C i-Csalkyloxy, and aminocarbonyl-C i-C4alkylene; R2 is selected from hydrogen, Ci-Cgalkyl, C2-C8alkenyl, C2-Cgalkynyl, Ci-Cgalkylcarbonyl, Ci-C3alkoxycarbonyl, hydroxyl, C i-C3alkyloxy, and aminocarbonyl-Ci-C4alkylene; and C' and C2 are independently oxygen or sulfur; or an agrochemically acceptable salt thereof.

Preferably Q1 is a saturated 4-to 6-membered heterocyclic ring comprising one or two sulftir atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from =0, N-Z or CZZ2; to Z is hydrogen or cyano Z' is cyano Z2 is cyano or Z' and Z2, taken together, fomi a bridge -C(0)-0-CH2-C(0)-or -C(0)-S-CH2-C(0)-Q2 is a moiety of formula (11) Yl (II) y5y3 wherein Y1 is selected from Cl, Br, I, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, trifluoromethylsuffinyl, trifluoromethylsulfonyl or methoxymethyl Y' is selected from Cl, Br, 1, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl or methoxymethyl; Y' is heptafluoroprop-2-yl or nonafluorobut-2-yl xL is hydrogen, methoxy or halogen Xb is hydrogen, halogen or cyano R' is selected from hydrogen, , -Cgalkyl, C2-Csalkenyl, C2-Cgalkynyl, , -Cgalkykarbonyl, C,-Csalkoxycarbonyl, hydroxyl, C,-Csalkyloxy, and aminocarbonyl-C,-C4alkylene; R2 is selected from hydrogen, C i-Cgalkyl, C2-Csalkenyl, C2-Cgalkynyl, C 1-Cgalkylcarbonyl, Ci-C8alkoxycarbonyl, hydroxyl, C i-C8alkyloxy, and aminocarbonyl-Ci-C4alkylene; and C' and C2 are both oxygen; More preferably Q' is a saturated 4-to 6-membered heterocyclic ring comprising one or two sulftir atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from 0, N-Z or CZ'Z2; Z is hydrogen or cyano Z' is cyano Z2 is cyano or Z' and Z2, taken together, form a bridge -C(0)-0-CH2-C(0)-or -C(0)-S-CH2-C(0)-to Q2 is a moiety of formula (II) Yl (II) y5y3 wherein Y' is selected from Cl, Br, I, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl or methoxymethyl Y' is selected from Cl, Br, I, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, trifluoromethylsuffinyl, trifluoromethylsulfonyl or methoxymethyl Y3 is heptafluoroprop-2-yl or nonafluorobut-2-yl xa is hydrogen, methoxy or halogen XL is hydrogen, halogen or cyano R' is selected from hydrogen, Ci-Cgalkyl, C2-Csalkenyl, C2-Cgalkynyl, Ci-Cgalkylcarbonyl, C -Calkoxycarbonyl, hydroxyl, C -Calkyloxy, and aminocarbonyl-C -C4alkylene; R2 is selected from hydrogen, Ci-Cgalkyl, C2-Csalkenyl, C2-Cgalkynyl, Ci-Cgalkylcarbonyl, C-Calkoxycarbonyl, hydroxyl, C-Calkyloxy, and aminocarbonyl-C-C4alkylene; and 0' and 02 are both oxygen; Even more preferably Q' is a saturated 4-to 6-membered heterocyclic ring comprising one or two sulfur atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from =0, N-Z or CZ Z2; Z is hydrogen or cyano Z' is cyano Z2 is cyano or Z1 and Z2, taken together, form a bridge -C(0)-0-CH2-C(0)-or -C(0)-S-CH2-C(0)-Q2 is a moiety of formula (II) Yl (II) wherein Y1 is selected from Cl, Br, I, methyl, ethyl, methoxy, trifluoromethyl, dif'luoromethoxy, trill uoromethoxy, trill uoromethylthio, or methoxymethyl Y' is selected from Cl, Br, I, methyl, ethyl Y3 is heptafluoroprop-2-yl or nonafluorobut-2-yl X' is hydrogen, methoxy or halogen X' is hydrogen, halogen or cyano R1 is selected from hydrogen, C i-C5alkyl, C2-Csalkenyl, C2-Cgalkynyl, C 1-Cgalkykarbonyl, C i-Csalkoxycarbonyl, hydroxyl, C i-Csalkyloxy, and aminocarbonyl-C i-Calkylene; R2 is selected from hydrogen, Ci-Cgalkyl, C2-C8alkenyl, C2-Cgalkynyl, Ci-Cgalkylcarbonyl, -C8alkoxycarbonyl, hydroxyl, -C8alkyloxy, and aminocarbonyl-Ci -C alkylene; and G' and G2 are both oxygen; G and G2 are both oxygen; Preferably in this preferred embodiment R' is selected from hydrogen, Ci-Cgalkyl, C2-Cgalkenyl; B? is selected from hydrogen, Ci-Cgalkyl, C2-Cgalkenyl; More preferably in this preferred embodiment R' is selected from hydrogen or C1-C4alkyl; R2 is selected from hydrogen, Ci-C4alkyl; And most preferably in this preferred embodiment R1 is selected from hydrogen, methyl or ethyl; R2 is selected from hydrogen, methyl, ethyl; Preferably X' is hydrogen, methoxy or F Preferably Xb is hydrogen, or cyano to Preferably Y is selected from Cl, Br, I, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl or methoxymethyl More preferably Y' is selected from Cl, Br, 1, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy IS Most preferably Y' is selected from Cl, Br, methyl, ethyl; Preferably Y5 is selected from Cl, Br, I, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy, tn fluoromethoxy, trifluoromethylthio, trifluoromethyl sulfinyl, trifluoromethysulfonyl or methoxymethyl; More preferably Y5 is selected from Cl, Br, I, methyl, ethyl, methoxy, trifluoromethyl or Even more preferably Y5 is selected from Cl, Br, I, methyl, ethyl Most preferably Y5 is selected from Cl, Br, ethyl; In a preferred embodiment Q' is selected from thietane-3-yl, oxo4hietane-3-yl, dioxo- thietane-3-yl, dithiolane-4-yl, dithiolane-3-yI, tetrahydrothiopyran-4-yl, tetrahydrothiopyran- 3-yl, 1-oxo-thiane-4-yI, 1-oxo-thiane-3-yl, l,l-dioxo-thiane-4-yl, l,l-dioxo-thiane-3-yl, 2,4-dioxotetrahydrofuran-3-ylidene)thiane-4-y, 2,4-dioxotetrahydrofriran-3-ylidene)thiane-3-yl, I -(dicyanomethylene)thiane-4-yl, I -(dicyanomethylene)thiane-3-yl, I -imino-i -oxo-thiane-4- yl, 1-imino-1-oxo-thiane-3-yl, 1-cyanoimino 1-oxo-thiane-4-yl, 1-cyanoimino 1-oxo-thiane- 3-yl, thia-1-ylidene-4-yl ammonium and mean thian-i-ylidene-3-yl ammonium.

In a more preferred embodiment Q is selected from thietane-3-yl, oxo-thietane-3-yl, dioxo- thietane-3-yl, dithiolane-4-yl, tetrahydrothiopyran-4-yl, 1-oxo-thiane-4-yl, 1,1 -dioxo-thiane- 4-yl, 2,4-dioxotetrahydrofuran-3-ylidene)thiane-4-yl, I -(dicyanomethylene)thiane-4- carboxamide, 1-imino-1-oxo-thiane-4-carboxamide, 1 -cyanoimino 1 -oxo-thiane-4, thian-1-ylidene-4-yl ammonium Preferably in a further embodiment of the present invention provides a compound of formula (I) wherein Q' is a saturated 4-to 6-membered heterocyclic ring comprising one or two sulfur atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from 0, N-Z or CZ1Z2; Z is hydrogen or cyano to ZJ is cyano Z2 is cyano or Z1 and Z2, taken together, form a bridge -C0)-0-CH2-C0)-or -C(0)-S-CH2-C(0)-Y' is selected from Cl, Br, I, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy or methoxymethyl IS Y' is selected from Cl, Br, I, methyl, ethyl Y3 is heptafluoroprop-2-y or nonafluorobut-2-yl xa is hydrogen, methoxy or halogen Xb is hydrogen or cyano R' is selected from hydrogen, Ci-Csalkyl, C2-Csalkenyl; R2 is selected from hydrogen, Ci-Cgalkyl, C2-Cgalkenyl; and G and G2 are both oxygen; More preferably the present invention provides a compound of formula (I) wherein Q' is a saturated 4-to 6-membered heterocyclic ring comprising one or two sulfur atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from 0, =N-Z or CZ'Z2; Z is hydrogen or cyano Y is selected from Cl, Br, 1, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy Y5 is selected from Cl, Br, I, ethyl Y3 is hepta±luoroprop-2-yl X' is hydrogen, methoxy or halogen Xb is hydrogen R' is selected from hydrogen or C1-C4aHcyl; R2 is selected from hydrogen, Ci-C4alkyl; and G' and G2 are both oxygen; Even more preferably the present invention provides a compound of formula (1) wherein Q' is a saturated 4-to 6-membered heterocyclic ring comprising one or two sulfur atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from =0; Y1 is selected from Cl, Br, methyl, ethyl; Y5 is selected from Cl, Br, ethyl; to Y' is heptafluoroprop-2-yl; xa is methoxy or F; Xb is hydrogen; R' is selected from hydrogen or Ci-C4alkyl; R2 is selected from hydrogen, Ci-C4alkyl; and is C' and C2 are both oxygen; Most preferably the present invention provides a compound of formula (1) wherein Q' is a saturated 4-to 6-membered heterocyclic ring comprising one or two sulftir atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from =0; Y is selected from Cl, Br, methyl, ethyl; Y5 is selected from Cl, Br, ethyl; Y is heptafluoroprop-2-y; X' is methoxy or F; X' is hydrogen; R' is selected from hydrogen, methyl or ethyl; R2 is selected fi-om hydrogen, methyl, ethyl; and C' and C2 are both oxygen; In another further preferred embodiment the present invention provides a compound of formula (I) wherein Q is a saturated 4-to 6-membered heterocyclic ring comprising one or two sulfur atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from =0; -10-Y' is selected from Cl, Br, methyl, ethyl; Y5 is selected from Cl, Br, ethyl; Y3 is heptafluoroprop-2-yl; xa is F; Xb is hydrogen; R' is selected from hydrogen or Ci-C4alkyl; R2 is selected from hydrogen, Ci-C4alkyl; and 11 and G2 are both oxygen; to Preferably this further preferred embodiment provides a compound of formula (I) wherein Q' is a saturated 4-to 6-membered heterocyclic ring comprising one or two suiftir atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from =0; Y' is selected from Cl, Br, methyl, ethyl; IS Y' is selected from Cl, Br, ethyl; Y3 is heptafluoroprop-2-y X is F; Xb is hydrogen; R' is selected from hydrogen, methyl or ethyl; R2 is selected from hydrogen, methyl, ethyl; and G and G2 are both oxygen; In another further preferred embodiment the present invention provides a compound of formula (I) wherein Q' is a saturated 4-to 6-membered heterocyclic ring comprising one or two sulfur atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from =0; Y is selected from Cl, Br, methyl, ethyl; Y5 is selected from Cl, Br, ethyl; Y3 is heptafluoroprop-2-yl r is methoxy; Xb is hydrogen; R' is selected from hydrogen or C1-C4aHcyl; R2 is selected from hydrogen, Ci-C4alkyl; and -11-G' and G2 are both oxygen; Preferably this further prefered embodiment provides a compound of formula (I) wherein Q1 is a saturated 4-to 6-membered heterocyclic ring comprising one or two suiftir atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from =0; Y' is selected from Cl, Br, methyl, ethyl; Y is selected from Cl, Br, ethyl; Y' is heptatluoroprop-2-yl to xa is methoxy; Xb is hydrogen; R1 is selected from hydrogen, methyl or ethyl; R2 is selected from hydrogen, methyl, ethyl; and G' and G2 are both oxygen;

IS

In another further preferred embodiment the present invention provides a compound of formula (I) wherein Q' is a saturated 4-to 6-membered heterocyclic ring comprising one or two sulftir atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulftir atom with one or two substituents selected from =0; Y is selected from Cl, Br, methyl, ethyl; Y5 is selected from Cl, Br, ethyl; Y is heptafluoroprop-2-y; X' is hydrogen; Xb is cyano; R' is selected from hydrogen or C1-C4alkyl; R2 is selected fiom hydrogen, Ci-C4alkyl; and C' and C2 are both oxygen; Preferably this further prefered embodiment provides a compound of formula (I) wherein Q' is a saturated 4-to 6-membered heterocyclic ring comprising one or two sulfur atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from =0; Y1 is selected from Cl, Br, methyl, ethyl; -12 -Y5 is selected from Cl, Br, ethyl; Y3 is heptafluoroprop-2-yl; xa is hydrogen; Xb is cyano; R' is selected from hydrogen, methyl or ethyl; R2 is selected from hydrogen, methyl, ethyl; and G' and G2 are both oxygen; The present invention further relates to compounds according to the fonriula (V) Rç NAQ1 xç, wherein R is s&ected from OH, Ci-C6alkoxy, F, Cl or Br; Q1 is a saturated 4-to 6-membered heterocyclic ring comprising one or two sulftir atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom IS with one or two substituents selected from 0, N-Z or CZ'Z2; Z is hydrogen or cyano; Z' is cyano Z2 is cyano or Z' and Z2, taken together, form a bridge -C(O)-O-CH2-C(O)-or -C(O)-S-CH2-C(O)-; and the values of X", X' and R1 as set out above for the different embodiments of the present invention, or a salt thereof The present invention further relates to a process for the production of compounds according to the formula (I) or an agrochemically acceptable salt thereof characterized in that a compound according to the formula (V) -13 -

R NQ xç

wherein R is selected from OF-I, C-C6a1koxy, Cl, F or Br and the values of x', X" and R' as set out above for the different embodiments of the present invention and Q1 is a saturated 4-to 6-membered heterocyclic ring comprising one or two suiftir atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from =0, =N-Z or =CZ1Z2; Z is hydrogen or cyano Z' iscyano Z2 is cyano or 7' and z2, taken together form a bridge -C(O)-O-CH2-C(O)-or -C(0)-S-CH2-C(O)-is reacted with and with an amine of formula NHR2Q2 wherein Q2 is a moiety of formula (II) Yl (II) and Y3 is heptafluoroprop-2-yl or nonafluorobut-2-yl 1(2, Y' and Y5 are, in any combination, as set out above for the different embodiments of the present invention.

The present invention further relates to the method of use of compounds according to the formula (V) -14 -

R NQ xç

for the production of compounds according to formula (lU) RNQ1 (III) N 2 wherein xa is hydrogen, methoxy or halogen X' is hydrogen, halogen or cyano R is s&ected from OH, Ci-Coalkoxy, Cl, F or Br and the values of Q1, Q2, R, R2, Y1 and Y5 as set out above for the different embodiments of the present invention or a salt thereof The present invention further relates to compounds according to the formula (IV) -OMe (IV) N1 wherein Xa is hydrogen, methoxy or halogen, Xb is hydrogen, halogen or cyano and R' is selected from methyl, ethyl, n-propyl and n-butyl, or a salt thereof The present invention further relates to the method of use of compounds according to the formula (IV) -15 -OMe xb>C (iv) N.N1 for the production of compounds according to formula (V) RcA, xcoç wherein X and R1 have the meaning as set out above for the different embodiments of the present invention and preferably R' is selected from methyl, ethyl, n-propyl and n-butyl, R is selected from OH, C1-C6alkoxy, Cl, F or Br and Q' is a saturated 4-to 6-membered heterocyclic ring containing one or two sulfur atoms or a salt thereof I0 The compounds in Tables I to 2 below illustrate the compounds of the invention.

80211 -GB-REG-ORG-NAT-1

Table I:

Table I provides 480 compounds of formula (III) wherein Q', Q2, R', R2, Xa and Xb have the values listed in the table below. (III)

Compound numbers X' 5r R' R2 1.1 F H Methyl H thietan-3-yl 2-ethyl-6-bromo-4-(heptatluoroprop-2-yl)phenyl 1.2 F H Methyl H thietan-3-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.3 F H Methyl H thietan-3-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.4 F H Methyl H thietan-3-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.5 F H Methyl H thietan-3-yl 2,6-dichloro-4-(heptatluoroprop-2-yl)phenyl 1.6 F H Methyl H thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.7 F H Methyl H thietan-3 -yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.8 F H Methyl H thietan-3 -yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.9 F H Methyl H dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 Compound numbers X1 -5r R' 1.10 F H Methyl H dithiolan-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1. 11 F H Methyl H dithiolan-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.12 F H Methyl H dithiolan-4-yl 2-bromo-6-chloro-4-(heptatluoroprop-2-yl)phenyl 13 F H Methyl H dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 14 F H Methyl H dithiolan-4-yl 2,6-dibromo-4-(heptatluoroprop-2-yl)phenyl 1 F H Methyl H dithiolan-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.16 F H Methyl H dithiolan-4-yl 2-brorno-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.17 F H Methyl H tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1. 18 F H Methyl I-I tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.19 F H Methyl H tetrahydrothiopyran-4-yl 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-y)phenyl 1.20 F H Methyl H tetrahydrothiopyran-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.21 F H Methyl H tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.22 F H Methyl H tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.23 F H Methyl H tetrahydrothiopyran-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.24 F H Methyl H tetrahydrothiopyran-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.25 F H Ethyl H thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.26 F H Ethyl H thietan-3-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.27 F H Ethyl H thietan-3-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.28 F H Ethyl H thietan-3-yl 2-bromo-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.29 F H Ethyl H thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 Compound numbers X1 -5r R' 1.30 F H Ethyl H thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.31 F H Ethyl H thietan-3-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.32 F H Ethyl H thietan-3-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.33 F H Ethyl H dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.34 F H Ethyl H dithiolan-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.35 F H Ethyl H dithiolan-4-yl 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.36 F H Ethyl H dithiolan-4-yl 2-brorno-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.37 F H Ethyl H dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.38 F H Ethyl I-I dithiolan-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.39 F H Ethy' H dithiolan-4-yI 2-choro-6-methy-4-(heptafluoroprop-2-yI)pheny 1.40 F H Ethy' H dithiolan-4-yI 2-bromo-6-methy-4-(heptafluoroprop-2-yI)pheny 1.41 F H Ethyl H tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.42 F H Ethyl H tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.43 F H Ethyl H tetrahydrothiopyran-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.44 F H Ethyl H tetrahydrothiopyran-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.45 F H Ethyl H tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.46 F H Ethyl H tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.47 F H Ethyl H tetrahydrothiopyran-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.48 F H Ethyl H tetrahydrothiopyran-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.49 F H n-Propyl H thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1

I I

Compound numbers X X R Q Q 1.50 F H n-Propyl H thietan-3-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.51 F H n-Propyl H thietan-3 -yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.52 F H n-Propyl H thietan-3-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.53 F H n-Propyl H thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.54 F H n-Propyl H thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.55 F H n-Propyl H thietan-3-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.56 F H n-Propyl H thietan-3 -yl 2-brorno-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.57 F H n-Propyl H dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.58 F H n-Propyl I-I dithiolan-4-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.59 F H n-Propyl H dithiolan-4-yI 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-y)phenyl 1.60 F H n-Propyl H dithiolan-4-yI 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.61 F H n-Propyl H dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.62 F H n-Propyl H dithiolan-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.63 F H n-Propyl H dithiolan-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.64 F H n-Propyl H dithiolan-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.65 F H n-Propyl H tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.66 F H n-Propyl H tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.67 F H n-Propyl H tetrahydrothiopyran-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.68 F H n-Propyl H tetrahydrothiopyran-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.69 F H n-Propyl H tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -20 -Compound numbers X1 jr R' 1.70 F H n-Propyl H tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.71 F H n-Propyl H tetrahydrothiopyran-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.72 F H n-Propyl H tetrahydrothiopyran-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.73 F H H H thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.74 F H H H thietan-3-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.75 F H H H thietan-3-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.76 F H H H thietan-3-yl 2-brorno-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.77 F H H H thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.78 F H H I-I thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.79 F H H H thietan-3 -y 2-choro-6-methy-4-(heptafluoroprop-2-yI)pheny 1.80 F H H H thietan-3-y 2-bromo-6-methy-4-(heptafluoroprop-2-yI)pheny 1.81 F H H H dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.82 F H H H dithiolan-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.83 F H H H dithiolan-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.84 F H H H dithiolan-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.85 F H H H dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.86 F H H H dithiolan-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.87 F H H H dithiolan-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.88 F H H H dithiolan-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.89 F H H H tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -21 -Compound numbers X1 -5r R' 1.90 F H H H tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.91 F H H H tetrahydrothiopyran-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.92 F H H H tetrahydrothiopyran-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.93 F H H H tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.94 F H H H tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptatluoroprop-2-yl)phenyl 1.95 F H H H tetrahydrothiopyran-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.96 F H H H tetrahydrothiopyran-4-yl 2-brorno-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.97 F H Methyl Methyl thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.98 F H Methyl Methyl thietan-3-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.99 F H Methyl Methyl thietan-3-yl 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.100 F H Methyl Methyl thietan-3-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.101 F H Methyl Methyl thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.102 F H Methyl Methyl thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.103 F H Methyl Methyl thietan-3-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.104 F H Methyl Methyl thietan-3-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl F H Methyl Methyl dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.106 F H Methyl Methyl dithiolan-4-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.107 F H Methyl Methyl dithiolan-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 108 F H Methyl Methyl dithiolan-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 109 F H Methyl Methyl dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -22 -Compound numbers Xa -5r R' 1.110 F H Methyl Methyl dithiolan-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1. 111 F H Methyl Methyl dithiolan-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1. 112 F H Methyl Methyl dithiolan-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 113 F H Methyl Methyl tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 114 F H Methyl Methyl tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl F H Methyl Methyl tetrahydrothiopyran-4-yl 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.116 F H Methyl Methyl tetrahydrothiopyran-4-yl 2-brorno-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.117 F H Methyl Methyl tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.118 F H Methyl Methyl tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.119 F H Methyl Methy' tetrahydrothiopyran-4-yl 2-choro-6-methy-4-(heptafluoroprop-2-yI)pheny 1. 120 F H Methyl Methy' tetrahydrothiopyran-4-yl 2-bromo-6-methy-4-(heptafluoroprop-2-yI)pheny 1.121 H H Methyl H thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.122 H H Methyl H thietan-3-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.123 H H Methyl H thietan-3-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.124 H H Methyl H thietan-3-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.125 H H Methyl H thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.126 H H Methyl H thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.127 H H Methyl H thietan-3-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.128 H H Methyl H thietan-3-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 129 H H Methyl H dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -23 -Compound numbers X1 -5r R' 1.130 H H Methyl H dithiolan-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.131 H H Methyl H dithiolan-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.132 H H Methyl H dithiolan-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yflphenyl 1.133 H H Methyl H dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 134 H H Methyl H dithiolan-4-yl 2,6-dibromo-4-(heptatluoroprop-2-yl)phenyl 1.135 H H Methyl H dithiolan-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.136 H H Methyl H dithiolan-4-yl 2-brorno-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.137 H H Methyl H tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.138 H H Methyl H tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.139 H H Methyl H tetrahydrothiopyran-4-yl 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-y)phenyl 1.140 H H Methyl H tetrahydrothiopyran-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.141 H H Methyl H tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.142 H H Methyl H tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 143 H H Methyl H tetrahydrothiopyran-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 144 H H Methyl H tetrahydrothiopyran-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.145 H H Ethyl H thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.146 H H Ethyl H thietan-3-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.147 H H Ethyl H thietan-3-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.148 H H Ethyl H thietan-3-yl 2-bromo-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.149 H H Ethyl H thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -24 -Compound numbers X1 -5r R' 1.150 H H Ethyl H thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1. 151 H H Ethyl H thietan-3 -yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1. 152 H H Ethyl H thietan-3 -yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl I H H Ethyl H dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl I 54 H H Ethyl H dithiolan-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl I 55 H H Ethyl H dithiolan-4-yl 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1. 156 H H Ethyl H dithiolan-4-yl 2-brorno-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1. 157 H H Ethyl H dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.158 H H Ethyl H dithiolan-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1. 159 H H Ethy' H dithiolan-4-yI 2-choro-6-methy-4-(heptafluoroprop-2-yI)pheny 1.160 H H Ethy' H dithiolan-4-yI 2-bromo-6-methy-4-(heptafluoroprop-2-yI)pheny 1.161 H H Ethyl H tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.162 H H Ethyl H tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl I. 163 H H Ethyl H tetrahydrothiopyran-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl I. 164 H H Ethyl H tetrahydrothiopyran-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl I. I 65 H H Ethyl H tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.166 H H Ethyl H tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.167 H H Ethyl H tetrahydrothiopyran-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl I. 168 H H Ethyl H tetrahydrothiopyran-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.169 H H n-Propyl H thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -25 -Compound numbers X1 jr R' 1.170 H H n-Propyl H thietan-3-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1. 171 H H n-Propyl H thietan-3 -yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.172 H H n-Propyl H thietan-3-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.173 H H n-Propyl H thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.174 H H n-Propyl H thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.175 H H n-Propyl H thietan-3-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.176 H H n-Propyl H thietan-3-yl 2-brorno-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.177 H H n-Propyl H dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.178 H H n-Propyl H dithiolan-4-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.179 H H n-Propyl H dithiolan-4-yI 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-y)phenyl 1.180 H H n-Propyl H dithiolan-4-yI 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1. 181 H H n-Propyl H dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1. 182 H H n-Propyl H dithiolan-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1 83 H H n-Propyl H dithiolan-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1 84 H H n-Propyl H dithiolan-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1 85 H H n-Propyl H tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1. 186 H H n-Propyl H tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1. 187 H H n-Propyl H tetrahydrothiopyran-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1 88 H H n-Propyl H tetrahydrothiopyran-4-yl 2-bromo-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1 89 H H n-Propyl H tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -26 -a I I Compound numbers X X R R Q Q 1.190 H H n-Propyl H tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.191 H H n-Propyl H tetrahydrothiopyran-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.192 H H n-Propyl H tetrahydrothiopyran-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.193 H H H H thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.194 H H H H thietan-3-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.195 H H H H thietan-3-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.196 H H H H thietan-3-yl 2-brorno-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.197 H H H H thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.198 H H H I-I thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.199 H H H H thietan-3-y 2-choro-6-methy-4-(heptafluoroprop-2-yI)pheny 1.200 H H H H thietan-3-y 2-bromo-6-methy-4-(heptafluoroprop-2-yI)pheny 1.201 H H H H dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.202 H H H H dithiolan-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.203 H H H H dithiolan-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.204 H H H H dithiolan-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.205 H H H H dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.206 H H H H dithiolan-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.207 H H H H dithiolan-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.208 H H H H dithiolan-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.209 H H H H tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -27 -Compound numbers X1 -5r R' 1.210 H H H H tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.211 H H H H tetrahydrothiopyran-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.212 H H H H tetrahydrothiopyran-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.213 H H H H tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.214 H H H H tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptatluoroprop-2-yl)phenyl 1.215 H H H H tetrahydrothiopyran-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.216 H H H H tetrahydrothiopyran-4-yl 2-brorno-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.217 H H Methyl Methyl thietan-3 -yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.218 H H Methyl Methyl thietan-3 -yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.219 H H Methyl Methyl thietan-3 -yl 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.220 H H Methyl Methyl thietan-3 -yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.221 H H Methyl Methyl thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.222 H H Methyl Methyl thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.223 H H Methyl Methyl thietan-3-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.224 H H Methyl Methyl thietan-3-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.225 H H Methyl Methyl dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.226 H H Methyl Methyl dithiolan-4-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.227 H H Methyl Methyl dithiolan-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.228 H H Methyl Methyl dithiolan-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.229 H H Methyl Methyl dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -28 -Compound numbers X1 -5r R' 1.230 H H Methyl Methyl dithiolan-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.231 H H Methyl Methyl dithiolan-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.232 H H Methyl Methyl dithiolan-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.233 H H Methyl Methyl tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.234 H H Methyl Methyl tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.235 H H Methyl Methyl tetrahydrothiopyran-4-yl 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.236 H H Methyl Methyl tetrahydrothiopyran-4-yl 2-brorno-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.237 H H Methyl Methyl tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.238 H H Methyl Methyl tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.239 H H Methyl Methy' tetrahydrothiopyran-4-yl 2-choro-6-methy-4-(heptafluoroprop-2-yI)pheny 1.240 H H Methyl Methy' tetrahydrothiopyran-4-yl 2-bromo-6-methy-4-(heptafluoroprop-2-yI)pheny 1.241 Methoxy H Methyl H thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.242 Methoxy H Methyl H thietan-3-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.243 Methoxy H Methyl H thietan-3-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.244 Methoxy H Methyl H thietan-3-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.245 Methoxy H Methyl H thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.246 Methoxy H Methyl H thietan-3 -yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.247 Methoxy H Methyl H thietan-3-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.248 Methoxy H Methyl H thietan-3-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.249 Methoxy H Methyl H dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -29 -Compound numbers X1 -5r R' 1.250 Methoxy H Methyl H dithiolan-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.251 Methoxy H Methyl H dithiolan-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.252 Methoxy H Methyl H dithiolan-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yflphenyl 1.233 Methoxy H Methyl H dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.254 Methoxy H Methyl H dithiolan-4-yl 2,6-dibromo-4-(heptatluoroprop-2-yl)phenyl 1.255 Methoxy H Methyl H dithiolan-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.256 Methoxy H Methyl H dithiolan-4-yl 2-brorno-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.257 Methoxy H Methyl H tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.258 Methoxy H Methyl I-I tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.259 Methoxy H Methyl H tetrahydrothiopyran-4-yl 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-yphenyl 1.260 Methoxy H Methyl H tetrahydrothiopyran-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.261 Methoxy H Methyl H tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.262 Methoxy H Methyl H tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.263 Methoxy H Methyl H tetrahydrothiopyran-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.264 Methoxy H Methyl H tetrahydrothiopyran-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.265 Methoxy H Ethyl H thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.266 Methoxy H Ethyl H thietan-3-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.267 Methoxy H Ethyl H thietan-3-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.268 Methoxy H Ethyl H thietan-3-yl 2-bromo-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.269 Methoxy H Ethyl H thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -30 -Compound numbers X1 jr R' 1.270 Methoxy H Ethyl H thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.271 Methoxy H Ethyl H thietan-3-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.272 Methoxy H Ethyl H thietan-3-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.273 Methoxy H Ethyl H dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.274 Methoxy H Ethyl H dithiolan-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.275 Methoxy H Ethyl H dithiolan-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.276 Methoxy H Ethyl H dithiolan-4-yl 2-brorno-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.277 Methoxy H Ethyl H dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.278 Methoxy H Ethyl I-I dithiolan-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.279 Methoxy H Ethyl H dithiolan-4-yI 2-chloro-6-methyl-4-(heptafluoroprop-2-yI)phenyl 1.280 Methoxy H Ethyl H dithiolan-4-yI 2-bromo-6-methyl-4-(heptafluoroprop-2-yI)phenyl 1.281 Methoxy H Ethyl H tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.282 Methoxy H Ethyl H tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.283 Methoxy H Ethyl H tetrahydrothiopyran-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.284 Methoxy H Ethyl H tetrahydrothiopyran-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.285 Methoxy H Ethyl H tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.286 Methoxy H Ethyl H tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.287 Methoxy H Ethyl H tetrahydrothiopyran-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.288 Methoxy H Ethyl H tetrahydrothiopyran-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.289 Methoxy H n-Propyl H thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -3 -Compound numbers X1 jr R' 1.290 Methoxy H n-Propyl H thietan-3-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.291 Methoxy H n-Propyl H thietan-3-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.292 Methoxy H n-Propyl H thietan-3-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.293 Methoxy H n-Propyl H thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.294 Methoxy H n-Propyl H thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.295 Methoxy H n-Propyl H thietan-3-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.296 Methoxy H n-Propyl H thietan-3-yl 2-brorno-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.297 Methoxy H n-Propyl H dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.298 Methoxy H n-Propyl I-I dithiolan-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.299 Methoxy H n-Propyl H dithiolan-4-yI 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-y)phenyl 1.300 Methoxy H n-Propyl H dithiolan-4-yI 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.301 Methoxy H n-Propyl H dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.302 Methoxy H n-Propyl H dithiolan-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.303 Methoxy H n-Propyl H dithiolan-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.304 Methoxy H n-Propyl H dithiolan-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.305 Methoxy H n-Propyl H tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.306 Methoxy H n-Propyl H tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.307 Methoxy H n-Propyl H tetrahydrothiopyran-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.308 Methoxy H n-Propyl H tetrahydrothiopyran-4-yl 2-bromo-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.309 Methoxy H n-Propyl H tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -32 -Compound numbers X1 jr R' 1.310 Methoxy H n-Propyl H tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.311 Methoxy H n-Propyl H tetrahydrothiopyran-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.312 Methoxy H n-Propyl H tetrahydrothiopyran-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.313 Methoxy H H H thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.314 Methoxy H H H thietan-3 -yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.315 Methoxy H H H thietan-3-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.316 Methoxy H H H thietan-3-yl 2-brorno-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.317 Methoxy H H H thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.318 Methoxy H H H thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.319 Methoxy H H H thietan-3-y 2-choro-6-methy-4-(heptafluoroprop-2-yI)pheny 1.320 Methoxy H H H thietan-3-y 2-bromo-6-methy-4-(heptafluoroprop-2-yI)pheny 1.321 Methoxy H H H dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.322 Methoxy H H H dithiolan-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.323 Methoxy H H H dithiolan-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.324 Methoxy H H H dithiolan-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.325 Methoxy H H H dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.326 Methoxy H H H dithiolan-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.327 Methoxy H H H dithiolan-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.328 Methoxy H H H dithiolan-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.329 Methoxy H H H tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -33 -Compound numbers X1 -5r R' 1.330 Methoxy H H H tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.331 Methoxy H H H tetrahydrothiopyran-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.332 Methoxy H H H tetrahydrothiopyran-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.333 Methoxy H H H tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.334 Methoxy H H H tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptatluoroprop-2-yl)phenyl 1.335 Methoxy H H H tetrahydrothiopyran-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.336 Methoxy H H H tetrahydrothiopyran-4-yl 2-brorno-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.337 Methoxy H Methyl Methyl thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.338 Methoxy H Methyl Methyl thietan-3 -yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.339 Methoxy H Methyl Methyl thietan-3 -yl 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.340 Methoxy H Methyl Methyl thietan-3 -yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.341 Methoxy H Methyl Methyl thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.342 Methoxy H Methyl Methyl thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.343 Methoxy H Methyl Methyl thietan-3-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.344 Methoxy H Methyl Methyl thietan-3-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.345 Methoxy H Methyl Methyl dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.346 Methoxy H Methyl Methyl dithiolan-4-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.347 Methoxy H Methyl Methyl dithiolan-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.348 Methoxy H Methyl Methyl dithiolan-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.349 Methoxy H Methyl Methyl dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -34 -Compound numbers X1 -5r R' 1.350 Methoxy H Methyl Methyl dithiolan-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.351 Methoxy H Methyl Methyl dithiolan-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.352 Methoxy H Methyl Methyl dithiolan-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.353 Methoxy H Methyl Methyl tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.354 Methoxy H Methyl Methyl tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.355 Methoxy H Methyl Methyl tetrahydrothiopyran-4-yl 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.356 Methoxy H Methyl Methyl tetrahydrothiopyran-4-yl 2-brorno-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.357 Methoxy H Methyl Methyl tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.358 Methoxy H Methyl Methyl tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.359 Methoxy H Methyl Methy' tetrahydrothiopyran-4-yl 2-choro-6-methy-4-(heptafluoroprop-2-yI)pheny 1.360 Methoxy H Methyl Methy' tetrahydrothiopyran-4-yl 2-bromo-6-methy-4-(heptafluoroprop-2-yI)pheny 1.361 H CN Methyl H thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.362 H CN Methyl H thietan-3-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.363 H CN Methyl H thietan-3-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.364 H CN Methyl H thietan-3-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.365 H CN Methyl H thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.366 H CN Methyl H thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.367 H CN Methyl H thietan-3-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.368 H CN Methyl H thietan-3-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.369 H CN Methyl H dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -35 -Compound numbers Xa -5r R' 1.370 H CN Methyl H dithiolan-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.371 H CN Methyl H dithiolan-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.372 H CN Methyl H dithiolan-4-yl 2-bromo-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.373 H CN Methyl H dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.374 H CN Methyl H dithiolan-4-yl 2,6-dibromo-4-(heptatluoroprop-2-yl)phenyl 1.375 H CN Methyl H dithiolan-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.376 H CN Methyl H dithiolan-4-yl 2-brorno-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.377 H CN Methyl H tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.378 H CN Methyl H tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.379 H CN Methyl H tetrahydrothiopyran-4-yl 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-y)phenyl 1.380 H CN Methyl H tetrahydrothiopyran-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.381 H CN Methyl H tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.382 H CN Methyl H tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.383 H CN Methyl H tetrahydrothiopyran-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.384 H CN Methyl H tetrahydrothiopyran-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.385 H CN Ethyl H thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.386 H CN Ethyl H thietan-3-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.387 H CN Ethyl H thietan-3-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.388 H CN Ethyl H thietan-3-yl 2-bromo-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.389 H CN Ethyl H thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -36 -Compound numbers Xa jr R' 1.390 H CN Ethyl H thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.391 H CN Ethyl H thietan-3-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.392 H CN Ethyl H thietan-3-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.393 H CN Ethyl H dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.394 H CN Ethyl H dithiolan-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.395 H CN Ethyl H dithiolan-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.396 H CN Ethyl H dithiolan-4-yl 2-brorno-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.397 H CN Ethyl H dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.398 H CN Ethyl I-I dithiolan-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.399 H CN Ethyl H dithiolan-4-yI 2-chloro-6-methyl-4-(heptafluoroprop-2-yI)phenyl 1.400 H CN Ethyl H dithiolan-4-yI 2-bromo-6-methyl-4-(heptafluoroprop-2-yI)phenyl 1.401 H CN Ethyl H tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.402 H CN Ethyl H tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.403 H CN Ethyl H tetrahydrothiopyran-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.404 H CN Ethyl H tetrahydrothiopyran-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.405 H CN Ethyl H tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.406 H CN Ethyl H tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.407 H CN Ethyl H tetrahydrothiopyran-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.408 H CN Ethyl H tetrahydrothiopyran-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.409 H CN n-Propyl H thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -37 -Compound numbers Xa jr R' 1.410 H CN n-Propyl H thietan-3-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.411 H CN n-Propyl H thietan-3-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.4 12 H CN n-Propyl H thietan-3-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.413 H CN n-Propyl H thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.414 H CN n-Propyl H thietan-3-yl 2,6-dibromo-4-(heptatluoroprop-2-yl)phenyl 1.415 H CN n-Propyl H thietan-3-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.416 H CN n-Propyl H thietan-3 -yl 2-brorno-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.4 17 H CN n-Propyl H dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.418 H CN n-Propyl H dithiolan-4-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.419 H CN n-Propyl H dithiolan-4-yI 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-y)phenyl 1.420 H CN n-Propyl H dithiolan-4-yI 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.421 H CN n-Propyl H dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.422 H CN n-Propyl H dithiolan-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.423 H CN n-Propyl H dithiolan-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.424 H CN n-Propyl H dithiolan-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.425 H CN n-Propyl H tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.426 H CN n-Propyl H tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.427 H CN n-Propyl H tetrahydrothiopyran-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.428 H CN n-Propyl H tetrahydrothiopyran-4-yl 2-bromo-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.429 H CN n-Propyl H tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -3 -a I I Compound numbers X X R R Q Q 1.430 H CN n-Propyl H tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.431 H CN n-Propyl H tetrahydrothiopyran-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.432 H CN n-Propyl H tetrahydrothiopyran-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.433 H CN H H thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.434 H CN H H thietan-3-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.435 H CN H H thietan-3-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.436 H CN H H thietan-3-yl 2-brorno-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.437 H CN H H thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.438 H CN H H thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.439 H CN H H thietan-3 -y 2-choro-6-methy-4-(heptafluoroprop-2-yI)pheny 1.440 H CN H H thietan-3-y 2-bromo-6-methy-4-(heptafluoroprop-2-yI)pheny 1.441 H CN H H dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.442 H CN H H dithiolan-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.443 H CN H H dithiolan-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.444 H CN H H dithiolan-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.445 H CN H H dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.446 H CN H H dithiolan-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.447 H CN H H dithiolan-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.448 H CN H H dithiolan-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.449 H CN H H tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -39 -Compound numbers Xa -5r R' 1.450 H CN H H tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.451 H CN H H tetrahydrothiopyran-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.452 H CN H H tetrahydrothiopyran-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.453 H CN H H tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.454 H CN H H tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptatluoroprop-2-yl)phenyl 1.455 H CN H H tetrahydrothiopyran-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.456 H CN H H tetrahydrothiopyran-4-yl 2-brorno-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.457 H CN Methyl Methyl thietan-3-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.458 H CN Methyl Methyl thietan-3 -yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.459 H CN Methyl Methyl thietan-3 -yl 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.460 H CN Methyl Methyl thietan-3 -yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.461 H CN Methyl Methyl thietan-3-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.462 H CN Methyl Methyl thietan-3-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.463 H CN Methyl Methyl thietan-3-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.464 H CN Methyl Methyl thietan-3-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.465 H CN Methyl Methyl dithiolan-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.466 H CN Methyl Methyl dithiolan-4-yl 2-ethyl-6-chloro-4-(heptatluoroprop-2-yl)phenyl 1.467 H CN Methyl Methyl dithiolan-4-yl 2-ethyl-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.468 H CN Methyl Methyl dithiolan-4-yl 2-bromo-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.469 H CN Methyl Methyl dithiolan-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 80211 -GB-REG-ORG-NAT-1 -40 -Compound numbers Xa -5r R' 1.470 H CN Methyl Methyl dithiolan-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.471 H CN Methyl Methyl dithiolan-4-yl 2-chloro-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.472 H CN Methyl Methyl dithiolan-4-yl 2-bromo-6-methyl-4-(heptafluoroprop-2-yl)phenyl 1.473 H CN Methyl Methyl tetrahydrothiopyran-4-yl 2-ethyl-6-bromo-4-(heptafluoroprop-2-yl)phenyl 1.474 H CN Methyl Methyl tetrahydrothiopyran-4-yl 2-ethyl-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.475 H CN Methyl Methyl tetrahydrothiopyran-4-yl 2-ethyl-6-rnethyl-4-(heptafluoroprop-2-yl)phenyl 1.476 H CN Methyl Methyl tetrahydrothiopyran-4-yl 2-brorno-6-chloro-4-(heptafluoroprop-2-yl)phenyl 1.477 H CN Methyl Methyl tetrahydrothiopyran-4-yl 2,6-dichloro-4-(heptafluoroprop-2-yl)phenyl 1.478 H CN Methyl Methyl tetrahydrothiopyran-4-yl 2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl 1.479 H CN Methyl Methy' tetrahydrothiopyran-4-yl 2-choro-6-methy-4-(heptafluoroprop-2-yI)pheny 1.480 H CN Methyl Methy' tetrahydrothiopyran-4-yl 2-bromo-6-methy-4-(heptafluoroprop-2-yI)pheny

Table 2:

TaHe 2 provides 144 compounds of formu'a (9 wherein Q1, Xa, Xb, R' and R have the va'ues listed in the taHe b&ow, 80211 -GB-REG-ORG-NAT-1 -41 -(V)

R

Compound Xa Xb Q' R' R numbers 2.1 F H thietan-3-yl H OH 2.2 F H thietan-3-yl H Methoxy 2.3 F H thietan-3-yl H CI 2.4 F H dithiolan-4-yl H OH 2.5 F H dithiolan-4-yl H Methoxy 2.6 F H dithiolan-4-yl H Cl 2.7 F H tetrahydrothiopyran-4-yl H OH 2.8 F H tetrahydrothiopyran-4-yl H Methoxy 2.9 F H tetrahydrothiopyran-4-yl H Cl 2.10 F H thietan-3-yl Methyl OH 2.11 F H thietan-3-yl Methyl Methoxy 2.12 F H thietan-3-yl Methyl Cl 80211 -GB-REG-ORG-NAT-1 -42 -Compound Xa Xb Q1 R numbers 2.13 F H dithiolan-4-yl Methyl OH 214 F H dithioan-4-yI Methy' Methoxy 2.15 F H dithiolan-4-yl Methyl Cl 2.16 F H tetrahydrothiopyran-4-yl Methyl OH 2.17 F H tetrahydrothiopyran-4-yl Methyl Methoxy 2.18 F H tetrahydrothiopyran-4-yl Methyl Cl 2.19 F H thietan-3-yl Ethyl OH 2.20 F H thietan-3-yl Ethyl Methoxy 2.21 F H thietan-3-yl Ethyl Cl 2.22 F H dithiolan-4-yl Ethyl OH 2.23 F H dithiolan-4-yl Ethyl Methoxy 224 F H dithiolan-4-yl Ethyl Cl 225 F H tetrahydrothiopyran-4-yl Ethyl OH 226 F H tetrahydrothiopyran-4-yl Ethyl Methoxy 227 F H tetrahydrothiopyran-4-yl Ethyl Cl 228 F H thietan-3-y n-Propyl OH 229 F H thietan-3-yl n-Propyl Methoxy 230 F H thietan-3-yl n-Propyl Cl 2.31 F H dithiolan-4-yl n-Propyl OH 80211 -GB-REG-ORG-NAT-1 -43 -Compound Xa Xb Q1 R numbers 232 F H dithiolan-4-yl n-Propyl Methoxy 233 F H dithiolan-4-yI n-Propyl CI 234 F H tetrahydrothiopyran-4-yl n-Propyl OH 235 F H tetrahydrothiopyran-4-yl n-Propyl Methoxy 236 F H tetrahydrothiopyran-4-yl n-Propyl Cl 2.37 H H thietan-3-yl H OH 2.38 H H thietan-3-yl H Methoxy 2.39 H H thietan-3-yl H Cl 2.40 H H dithiolan-4-yl H OH 2.41 H H dithiolan-4-yl H Methoxy 2.42 H H dithiolan-4-yl H Cl 2.43 H H tetrahydrothiopyran-4-yl H OH 2,44 H H tetrahydrothiopyran-4-yl H Methoxy 2.45 H H tetrahydrothiopyran-4-yl H Cl 2.46 H H thietan-3-yl Methyl OH 2.47 H H thietan-3-yl Methyl Methoxy 2.48 H H thietan-3-yl Methyl CI 2.49 H H dithiolan-4-yl Methyl OH 2.50 H H dithiolan-4-yl Methyl Methoxy 80211 -GB-REG-ORG-NAT-1 -44 -Compound Xa Xb Q1 R numbers 2.51 H H dithiolan-4-yl Methyl Cl 2.52 H H tetrahydrothiopyran-4-y Methy' OH 2.53 H H tetrahydrothiopyran-4-yl Methyl Methoxy 2.54 H H tetrahydrothiopyran-4-yl Methyl Cl 2.55 H H thietan-3-yl Ethyl OH 2.56 H H thietan-3-yl Ethyl Methoxy 2.57 H H thietan-3-yl Ethyl Cl 2.58 H H dithiolan-4-yl Ethyl OH 2.59 H H dithiolan-4-yl Ethyl Methoxy 2.60 H H dithiolan-4-yl Ethyl Cl 2.61 H H tetrahydrothiopyran-4-yl Ethyl OH 2,62 H H tetrahydrothiopyran-4-yl Ethyl Methoxy 2,63 H H tetrahydrothiopyran-4-yl Ethyl Cl 2.64 H H thietan-3-yl n-Propyl OH 2.65 H H thietan-3-yl n-Propyl Methoxy 2.66 H H thietan-3-y n-Propyl CI 2.67 H H dithiolan-4-yI n-Propyl OH 2.68 H H dithiolan-4-yl n-Propyl Methoxy 2.69 H H dithiolan-4-yl n-Propyl Cl 80211 -GB-REG-ORG-NAT-1 -45 -Compound Xa Xb Q1 R numbers 270 H H tetrahydrothiopyran-4-yl n-Propyl OH 271 H H tetrahydrothiopyran-4-yl n-Propyl Methoxy 272 H H tetrahydrothiopyran-4-yl n-Propyl Cl 273 Methoxy H thietan-3-yl H OH 274 Methoxy H thietan-3-yl H Methoxy 2.75 Methoxy H thietan-3-yl H Cl 2.76 Methoxy H dithiolan-4-yl H OH 2.77 Methoxy H dithiolan-4-yl H Methoxy 2.78 Methoxy H dithiolan-4-yl H Cl 2.79 Methoxy H tetrahydrothiopyran-4-yl H OH 2.80 Methoxy H tetrahydrothiopyran-4-yl H Methoxy 2.81 Methoxy H tetrahydrothiopyran-4-yl H Cl 2.82 Methoxy H thietan-3-yl Methyl OH 2,83 Methoxy H thietan-3-yl Methyl Methoxy 2.84 Methoxy H thietan-3-yl Methyl Cl 2.85 Methoxy H dithiolan-4-yI Methyl OH 2.86 Methoxy H dithiolan-4-yI Methyl Methoxy 2.87 Methoxy H dithiolan-4-yl Methyl Cl 2.88 Methoxy H tetrahydrothiopyran-4-yl Methyl OH 80211 -GB-REG-ORG-NAT-1 -46 -Compound Xa Xb Q1 R numbers 289 Methoxy H tetrahydrothiopyran-4-yl Methyl Methoxy 290 Methoxy H tetrahydrothiopyran-4-y Methy' CI 291 Methoxy H thietan-3-yl Ethyl OH 292 Methoxy H thietan-3-yl Ethyl Methoxy 293 Methoxy H thietan-3-yl Ethyl Cl 2.94 Methoxy H dithiolan-4-yl Ethyl OH 2.95 Methoxy H dithiolan-4-yl Ethyl Methoxy 2.96 Methoxy H dithiolan-4-yl Ethyl Cl 2.97 Methoxy H tetrahydrothiopyran-4-yl Ethyl OH 2.98 Methoxy H tetrahydrothiopyran-4-yl Ethyl Methoxy 2.99 Methoxy H tetrahydrothiopyran-4-yl Ethyl Cl 2.100 Methoxy H thietan-3-yl n-Propyl OH 2.101 Methoxy H thietan-3 -yl n-Propyl Methoxy 2.102 Methoxy H thietan-3-yl n-Propyl Cl 2.103 Methoxy H dithiolan-4-yl n-Propyl OH 2,104 Methoxy H dithiohn-4-yI n-Propyl Methoxy 2.105 Methoxy H dithiolan-4-yI n-Propyl CI 2.106 Methoxy H tetrahydrothiopyran-4-yl n-Propyl OH 2.107 Methoxy H tetrahydrothiopyran-4-yl n-Propyl Methoxy 80211 -GB-REG-ORG-NAT-1 -47 -Compound Xa Xb Q1 R numbers 2.108 Methoxy H tetrahydrothiopyran-4-yl n-Propyl Cl 2109 H CN thietan-3-yl H OH 2.110 H CN thietan-3-yl H Methoxy 2.111 H CN thietan-3-yl H Cl 2.112 H CN dithiolan-4-yl H OH 2.113 H CN dithiolan-4-yl H Methoxy 2.114 H CN dithiolan-4-yl H Cl 2.115 H CN tetrahydrothiopyran-4-yl H OH 2.116 H CN tetrahydrothiopyran-4-yl H Methoxy 2.117 H CN tetrahydrothiopyran-4-yl H Cl 2.118 H CN thietan-3-yl Methyl OH 2.119 H CN thietan-3-yl Methyl Methoxy 2,120 H CN thietan-3-yl Methyl Cl 2.121 H CN dithiolan-4-yl Methyl OH 2.122 H CN dithiolan-4-yl Methyl Methoxy 2.123 H CN dithiolan-4-yI Methyl CI 2.124 H CN tetrahydrothiopyran-4-yl Methyl OH 2.125 H CN tetrahydrothiopyran-4-yl Methyl Methoxy 2.126 H CN tetrahydrothiopyran-4-yl Methyl Cl 80211 -GB-REG-ORG-NAT-1 -48 -Compound Xa Xb Q1 R numbers 2127 H CN thietan-3-yl Ethyl OH 2128 H CN thietan-3-y Ethyl Methoxy 2129 H CN thietan-3-yl Ethyl Cl 2.130 H CN dithiolan-4-yl Ethyl OH 2.131 H CN dithiolan-4-yl Ethyl Methoxy 2.132 H CN dithiolan-4-yl Ethyl Cl 2.133 H CN tetrahydrothiopyran-4-yl Ethyl OH 2.134 H CN tetrahydrothiopyran-4-yl Ethyl Methoxy 2.135 H CN tetrahydrothiopyran-4-yl Ethyl Cl 2.136 H CN thietan-3-yl n-Propyl OH 2.137 H CN thietan-3-yl n-Propyl Methoxy 2.138 H CN thietan-3-yl n-Propyl Cl 2.139 H CN dithiolan-4-yl n-Propyl OH 2.140 H CN dithiolan-4-yl n-Propyl Methoxy 2,141 H CN dithiolan-4-yl n-Propyl Cl 2.142 H CN tetrahydrothiopyran-4-y n-Propyl OH 2.143 H CN tetrahydrothiopyran-4-yl n-Propyl Methoxy 2.144 H CN tetrahydrothiopyran-4-yl n-Propyl Cl -49 -The compounds of the invention may be made by a variety of methods, for example, the methods disclosed in WO 08/000438 or WO 2010/127928.

1) Compounds of formula (III) may be made by treatment of compounds of formula (V), wherein R is OH, Ci-C5alkoxy, Cl, F or Br with an amine of formula NI2Q2, When R is OH such reactions may be carried out in the presence of a coupling reagent, such as DCC (N,N'-dicyclohexylcarbodiimide), EDC (1 -ethyl-3 -[3 -dimethylamino-propyl]carbodiimide hydrochloride) or BOP-Cl (bis(2-oxo-3 -oxazolidinyl)phosphonic chloride), in the presence of a base, such as pyridine, triethylamine, 4-(dimethylamino)pyridine or to diisopropylethylamine, and optionally in the presence of a nucleophilic catalyst, such as hydroxybenzotriazole. When R is Cl, such reactions may be carried out under basic conditions, for example in the presence of pyridine, triethylamine, 4- (dimethylamino)pyridine or diisopropylethylamine, and optionally in the presence of a nucleophilic catalyst. Alternatively, the reaction may be conducted in a biphasic system IS comprising an organic solvent, preferably ethyl acetate, and an aqueous solvent, preferably a solution of sodium bicarbonate. When R is Ci-C6alkoxy the ester may be converted directly to the amide by heating the ester and amine together in a thermal process.

H

Xt%ç X (IV) (V) (III) 2) Acid halides of formula (V), wherein R is Cl, F or Br, may be made from carboxylic acids of formula (V), wherein R is OH by treatment with thionyl chloride or oxalyl chloride.

3) Carboxylic acids of formula (V), wherein R is OH, may be formed from esters of formula (V), wherein R is Ci-C6alkoxy by treatment of the ester with an alkali hydroxide, such as sodium hydroxide, in a solvent, such as ethanol.

4) Esters of formula (V), wherein R is Ci-C6alkoxy, may be made by treatment of compounds of formula (IV), wherein R is Cl-C(alkoxy, by acylation with a carboxylic acid -50 -of formula Q'-COOH or an acid halide of formula Q'-COHal, wherein Hal is Cl, F or Br, under standard conditions as described in 1), 5) Compounds of formula (IV), wherein P. is Ci-C6alkoxy, may be made from compounds of formula (VI) by sequential treatment with an alcohol R-OH under acidic conditions and then formation of the N-R' bond. For example, reductive amination may be achieved by treatment of the amine with an aldehyde or ketone and a reducing agent such as sodium cyanoborohydride. Alternatively, alkylation may be achieved by treating the amine with an alkylating agent such as an alkyl halide, optionally in the presence of a base. Alternatively, arylation may be achieved by treatment of the amine with an awl halide or sulfonate in the to presence of a suitable catalyst/ligand system, often a palladium (0) complex. NH2 (VI)

6) Alternatively, compounds of formula (IV), wherein R is Ci-C5alkoxy, may be made from a compound of formula (VII), wherein R is Ci-C6alkoxy and LG is a leaving group, such as bromo, chloro or sulfonate, via the displacement of the leaving group by an amine of formula R1-NH2 or other imine analogue followed by hydrolysis with a metal catalyst. See, for example: Chemical Communications (2009), (14), 189 1-1893 or Journal of Organic Chemistry (2000), 65(8), 2612-2614.

xçx xcjç (VIQ (I Compounds of formula (VII) and amines of formula R'-NH2 are either known compounds or may be made by methods known to a person skilled in the art.

6a) Alternatively, compounds of formula (IV), wherein R is C1-C6alkoxy, may be made from a compounds of formula XV, wherein R is Ci-C5alkoxy via reduction in the presence of a metal catalyst and a suitable two carbon building block such as acetaldehyde or acetonitrile. See for example: J. Org. Chem. 2007, 72, 9815 or Org. Left 2005, 7, 471 -51 -NO2 (IV) 7) Alternatively, compounds of formula (III), may be made by the treatment of compounds of formula (IX) with a carboxylic acid of formula Q-COOH or an acid halide of formula Q'-COHaI, wherein Hal is Cl, F or Br, under standard conditions as described in 1).

(IX) (lIE) 8) Compounds of formula (IX) may be formed from compounds of formula (VIII), wherein PG is a suitable protecting group and P. is OH, Cl or C-C6alkoxy, by amide bond formation with an amine of formula NHR2Q2 under standard conditions as described in 1), followed by removal of the protecting group P under standard conditions.

RLPG

xLJ..xa xL..<J<x8 _______xtJxa L2co

R R

(IV) (VIII) (IX) R 0 9) Compounds of formula (VIII), wherein R is OH or Ci-C6alkoxy, may be made by the protection of the amine functionality in compounds of formula (IV), wherein R is OH or is Ci-C6alkoxy, Suitable protecting groups include carbamates (such as (er/-butyloxycarbonyl, allyl oxycarbonyl and benzyl oxycarbonyl), tn alkyl silyl groups (such as tert-butyldimethyl-silyl) and acyl groups (such as acetyl).

-52 - 10) For compounds of formula (VIII) and compounds of formula (IV), the esters, wherein R is Ci-C6alkoxy, may be hydrolysed to the acids, wherein R is OH, by treatment with an alkali hydroxide, such as sodium hydroxide, in a solvent, such as ethanol. The acids may be converted to the acid chlorides, wherein R is Cl, by treatment with thionyl chloride or oxalyl chloride as described in 2) and 3).

ii) Alternatively, compounds of formula (IV), wherein R is OH, Cl, F, Br or Ci-Coalkoxy, may be converted directly to compounds of formula (IX) by amide bond formation with an amine of formula NHR2Q2 under standard conditions as described in 1), 12) Alternatively, compounds of formula (IX) may be made from compounds of to formula (XI), wherein LG is a leaving group such as iodo, bromo, chloro or sulfonate, by displacement of the leaving group with a compound of formula R'-NH2 or other imine analogue followed by hydrolysis with a metal catalyst. See for example: Chemical Communications (2009), (14), 1891-1893 or Journal of Organic Chemistry (2000), 65(8), 2612-2614.

is 13) Compounds of formula (XI) may be made from compounds of formula (X), wherein R is Cl or OH and LG is a leaving group as described in 12), via amide bond formation under standard conditions as described in fl, Compounds of formula (X) and formula (IV) are either known compounds or may be made by methods known to the person skilled in the art. xc)ç

(X) R (IX) 14) An alternative synthesis of compounds of formula (IX), wherein R1 is hydrogen, may be achieved by the reduction of nitro compounds of formula (XIII), such as by treatment with tin chloride under acidic conditions, or hydrogenation catalysed by a noble metal such as palladium on carbon, -53 -NO2 NO2 NH Xb F (XII) R (V) R22Q2 Yls LG or F 15) Compounds of formula (XIII) may be derived from compounds of formula (XII), wherein R is OH, Cl, or C-C6alkoxy, via acylation with an amine of formula NI-1R2Q2 under the standard conditions as described in 1).

16) For compounds of formula (XII), the esters, wherein R is Ci-C5alkoxy, may be hydrolysed to the acids, wherein P. is OH, by treatment with an alkali hydroxide, such as sodium hydroxide, in a solvent, such as ethanol as described in 3), The acids may be converted to the acid chlorides, wherein R is CI, by treatment with thionyl chloride or oxalyl chloride as described in 2). Compounds of formula (XII) are either known or may be made by methods known to a person skilled in the art.

17) Compounds of formula (XII) can be made from a compound of formula (XIV) wherein LU is a leaving group, such as diazonio or chlorine, by reaction with fluoride, such IS asKF, NO2 NO LG xb F

R R

(XW) (XII) The displacement of a halogen with a fluoride nucleophile can also be carried out on intermediates of formula (XIII) 18) Compounds of formula (XIII) where R2 is selected from Ci-Csalkyl, C2-Cgalkenyl, C2-Cgalkynyl, may be prepared from compounds of formula (XIII) where R2 is hydrogen, by treating them with a base, followed by an appropriate electrophile. Example of bases can be metal hydrides, like sodium hydride, potassium hydride or calcium hydride or -54 -metal alkoxide, like potassium t-butoxide, or organometals, like methyllithium, butyllithium, alkylmagnesium halide, metal amides like lithium diisopropylamide or lithium hexamethyldisilazide or a basic salt, like potassium carbonate. A solvent can be used. It could be, for example, a polar aprotic solvent like DTvIF or an ether like THF or dimethoxyethane. The reaction can be performed below 0°C or above 80°C, but preferably in DTVIF between 0°C and 25°C. The electrophile is R2-X' where R2 is selected from C1-Csalkyl, C2-Csalkeny, C2-C8alkynyl and X' is a leaving group like bromide, chloride, iodide, mesylate, trifiate, tosylate and the like. The base can be used in excess, as well as the electrophile, but preferably, the base is used in equivalent amounts as well as the to electrophilic reagent.

NO 2 NO2

xb Y Base,R2-X' y

(Example: I 0

N NaH,DMF,Me R2 2 (XIII) (XIII) (Yis LG, H 01 F xis leaving group (Y is LG or F = H) R2 different from H) 19) Compounds of formula (111) wherin Q' and Q2 are as defined in the description, IS R' is different from hydrogen and R2 is selected from Ci-C8alkyl, C2-C8alkenyl, C2-Csalkynyl, may be prepared from compound of formub (III) wherein Q1 and Q2 are as defined in the description, R1 is different from hydrogen and R2 is hydrogen, by treating it with a base, followed by an appropriate electrophile. Example of bases can be metal hydrides, like sodium hydride, potassium hydride or cakium hydride or metal alkoxide, like potassium t-butoxide, or orgariometals, like methyllithium, butyllithium, alkylmagnesium halide, metal amides like lithium diisopropylamide or lithium hexamethyldisilazide or a basic salt, like potassium carbonate. A solvent can be used. It could be, for example, a polar aprotic solvent like DMIF or an ether like THF or dimethoxyethane. The reaction can be performed below 0°C or above 80°C, but preferably in DMF between 0°C and 25°C, The electrophile is R2-X' where R2 is selected from Ci-Cgalkyl, C2-C5alkenyl, C2-CsaJ.kynyl and X' is a leaving group like bromide, chloride, iodide, mesylate, triflate, tosylate and the like.

The base can be used in excess, as well as the electrophile, but preferably, the base is used in -55 -equivalent amounts as well as the electrophilic reagent. Prefered conditions are sodium hydride in DMF between 0°C and 25°C.

xt_L._x Base, R2-X' 0 (mpIe: 0 NaH, DMF, Mel) (Il (Ill) (R1 not H R1 not H = H) Q(' is a Ieang group) not 1-0 20) Compounds of formula (III) wherin Q' and Q2 are as defined in the description, R' is selected from Ci-Csalkyl, C2-C8alkenyl, C2-Cgalkynyl and R2 is different from hydrogen, may be prepared from compound of formula (III) wherin Q1 and Q2 are as defined in the description, R is hydrogen and R2 is different from hydrogen, by treating it with a base, followed by an appropriate electrophile, Example of bases can be metal hydrides, like sodium hydride, potassium hydride or calcium hydride or metal alkoxide, like potassium t-butoxide, or organometals, like methyllithium, butyllithium, alkylmagnesium halide, metal amides like lithium diisopropylamide or lithium hexamethyldisilazide or a basic salt, like potassium carbonate. A solvent can be used. It could be, for example, a polar aprotic solvent like DMIF or an ether like uHF or dimethoxyethane. The reaction can be performed below 0°C or above 80°C, but preferably in DIVIF between 0°C and 25°C, The electrophile is R'-X' where R' is selected from Ci-C8alkyl, C2-Cgalkenyl, C2-C8alkynyl and X' is a leaving group like bromide, chloride, iodide, mesylate, triflate, tosylate and the like. The base can be used in excess, as well as the electrophile, but preferably, the base is used in equivalent amounts as well as the electrophilic reagent. Prefered conditions are sodium hydride in DMF between 0°Cand2S°C, -56 -R Jt N NaH, DMF, MeD R Q2 0") (III) (R1=H (R1notH R2 not H) (X isa leaving group) R2 not H) The compounds of formula (I) can be used to combat and control infestations of insect pests such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera, Hymenoptera and Isoptera and also other invertebrate pests, for example, acarine, nematode and mollusc pests. Insects, acarines, nematodes and molluscs are hereinafter collectively referred to as pests. The pests which may be combated and controlled by the use of the invention compounds include those pests associated with agriculture (which term includes the growing of crops for food and fiber products), horticulture and animal husbandry, companion animals, forestry and the storage of products of vegetable origin (such as fruit, grain and timber); those pests associated with the damage of man-made structures and the transmission of diseases of man and animals; and also nuisance pests (such as flies).

Examples of the abovementioned animal pests are: from the order Acarina, for example, Acalitus spp., Aculus spp., Acaricalus spp., Aceria spp., Acanis s/rn, Amblyomina spp., Argas spp., Booph/lus spp., Brevia1pus spp., Bryobia spp., (a1iitrimerus spp., (horioptes spp., Dermanyssus gal linac, Derinatophagoides spp,, Loletranychus spp,, Fr/ophyes spp,, J-Jemitarsonemus spp,, T-Tyalomrna spp,, Lvodes spp., Olygonychus spp., Omithodoros spp., Polyphagotarsone talus, Panonychus spp., Phyltocoplruta ofeivora, Phyionemnus spp., Polyp ha gotarsonein us spp., Psoroptes spp., Rhipicephatus spp,, Rhizoglyphits' spp,, Sarcoptes spp,, Steneoiarsonenus spp., Tarsonemus spp., and Tetranychus spp.; from the order Anopluro for example, I-Iaematopinus spp -, Linognathus spp., Peel/cu/us spp -, Pemphigus spp., and Phytloxera spp.; -57-from the order Co/cop/era, for example, Agriotes spp,, Ainphiinaiion majale, Anoinala orient ails, Anfhonoinus spp,, Aphodius' spp,, Astylus atronaculatus, Ataenius spp., Atomaria linearis, Chaetocnema tibia/is, Cerotoina spp., (onoderus spp -, Cosmopolites spp., (otinis nitida, (urcuilo spp., (yciocephala spp., Dermesles spp,, Diabro f/ca spp., Dilobodenis abderus, I4vilachna spp., Eremnus spp,, 1-Ic feronychus arator, Hypothenenius hampel, Lagria veiosa, Lept/notarsv decemLineata, Lissorhoptrus spp., Liogenys spp., Maecoiaspis spp., Maladera castanea, Megascelis spp., Melighefes aeneus, Ale lolontha spp,, Myochrous arma/us, Orycaephilus spp,, Ot/orhynchus spp., Phyl/ophaga spp., Phlyctinus spp,, Pop//i/a spp., Psyli/odes spp,, Rhyssornatus aubtilis, to Rhizopertha spp,, Scaraheidae, Sitophilus spp,, Sitotroga spp,, Sornaucus Spp., Shenophorus spp -, Siernechus subs/gnaws, Tenebrio spp., Tribolium spp., and Trogoclerma spp.; from the order D4p1 era, for example, IS Aedes spp., Anophe/es spp., Antherigona soccata, Bactrocea oleae, Bihio hortulanus, Bradysia spp., (ail4phora erythrocephaia, (era/it/s spp., (hrysoniyia spp., Cuiex spp., Cutere bra spp., Dacus spp., Del/a spp,, Drosophila melanogaster, i'thznia spp., Gastrophilus spp., Geomyza trzunctata, (7loswina spp., Hypoderina spp., ifyppohosca spp., Liriornyza spp., Inc//ia spp., Melanagrornyza spp., A4A'sca spp., Oesirus spp., Orseolia spp., Oscinei/a fr//, J'egomyia hyoscyami, l'horb/a spp., Rhagoie us spp., R/i'ei/a quadr/tàsc/ata, Scat ella spp., Sciara spp,, Stornoxys spp,, Tahanus spp., Tannia spp,, and F/pu/a spp,; from the order Hemitera, for example, Acanehocoris scahraf or, Acrosternurn spp,, A deiphocoris lineolaf ii. , Arnh/ype/ta ni/ida, Bathycoelia thaia&cina, Blissus spp, Cimex spp, (lavigralla tomentosico/ils, (reorniades spp., Distant/el/a theohroma, Diche/opsfiircatus, Dysdercus spp., /?dessa spp., Euchistus spp., Eni ydema puichnim, Luiygaster spp,, Halyomorpha haiys, Horcias nobi ic/ins, Lep-tocorisa spp,, Lygus spp,, Iviargarodes spp,, Ivhirgantia histrionic, ATeoinegalotornus spp,, Nesidiocoris tennis, Nezara spp., Ny's/us sirnu/ans, Oebaius insu/aris, Piesnia spp., Piezodorus spp,, Rhodnius spp., SahlbergeUa singularis, Scaptocoris castanea, Scolinophara spp., ihyanfa spp,, Iriatonja spp,, Vat/ga i/inc/ens; Acyrthosiurn pisuin, Adaiges spp., Agailiana ensigera, Agonoscena targioni/, Aleurodicus spp., Aleurocanthus spp,, Aleuroiobus barodensis, A/euro/brims /ioccosus, Aieyrodes -58-brassicae, Arnarasca b/gui/u/a, Arnr//odus at/c/i soni, Aonidie//a spp,, Aphid/c/ac, Aphis spp., Aspic/loins spp., Aulacorlhurn solanl, Baciericera cockere/li, Bern/s/a spp.. Brachycaudus spp., Brevicoryne hrciss/cae, Cacopsy/la spp., (avar/ella aegopodi Scop., Cerop/aster spp., Chrysomphalus aon/diurn, Chrysomphalus dictyosperrni, Cicade 1/a spp -, (ofàna spec ira, Crypt ornyzus spp,, Cicadu//na spp., Coccus hesper/durn, Dalbu/us maidis, Dia/eurodes spp,, Diaphorina ci/ri, Diuraph/s noxia, Dysaphis spp, Empoasca spp, Er/osoma lar/gerurn, Erythroneura spp., Gascardia spp., G/ycasp/s brirnbiecombei, Hyadaphispseudobrass/cae, JIya/oplerus spp, Ilyperornyzus pa//ic/us, idioscopus clypea/is, Jacobiasca lybica, Laodelphcex spp., Lecaniurn corn/, Lepidosaphes spp, Lopaphis erysimi, [yogenys maid/c, to IVacros/phurn spp., Itfahanarva spp, Ivfetcalfa pntinosa, IvIetopolophium dirhoc/urn, Myndus crudus, Myzus spp., Neotoxoptera spp., Nephotettix spp., Nilaparvaia spp., Nipoiachnus p/ri Mats, (*lonaspis ruthae, ()reguza lan/gera Zehnter, l'arabem/sia niyr/cae, Paratrioza cockere /1/, Par/a/aria spp, Pemphigus spp., Peregrinus maidts; Per/cit sic I/a spp., Phoroc/on humuli, Phy/loxera spp., Planococcus spp, Pseudauiacaspis spp, Pseudococcus spp, IS Pseuclatornoscelis seriattis, Psyila spp, Pu/vinaria act/i/op/ca, Ouadrasp/d/oius spp, Quesada gigas, Recilia dorsalis, Rhopaiosihurn spp -, Saisse I/a spp -, Scaphoideus spp., Schizaphis spp, S//oh/on spp., Sogaie//afurc/èra, ASpissisii/usfesiinus, larophagus Proserpina, Toxoptera spp, Tricileurodes spp., Tridiscus sporoho//, Trionymus spp., Triozci eiytreae, Unaspis c/tn, Zyg/na fiammigera, Zyg/nidia sat/el/arts; from the order [-[yrnenoptera, for example, Acromyrmex, Arge spp., A/ia spp., Cephus spp., Diprion spp, Diprionidae, (71/pin/a polytoma, Hoplocampa spp -, Las/us spp., Monom or/urn pharaonis, Neodin/on spp., Pogonomyrmex spp, S/enopsis in v/cia, So/enopsis spp., and Vèspa spp; from the order [sop/era, for examp'e, Coptoiermes spp., Corniternes curnulans, incisitermes spp, Iviacrotermes spp, &Iasioiermes spp., Microterrnes spp., Ret/cu/hermes spp; So/enopsis geminate from the order Lepidopiera, for example, Ac/er/s spp., Adoxophyes spp., Aegeria spp., Agrolis spp, A/abarna arg///aceae, Arny/o/s spp., Ant/cars/a gemmata/is, Archis spp., Argyresthia spp., Argyrotaetna spp, Autographa spp., Bucculutrix thurber/el/a, Busseolaflisca, (ac/ru can/c/ia, Carposina niponensis, (hi/a spp., Chor/sioneura spp, Chrysoleuchia lop/aria, Clysla ambigue//a, Cnapha/ocrocis spp., -59-Cnephasia spp., Cockylis spp., Coleophora spp., Colias lesbi4 Cosmophilaflav4 Crambus spp., Crocidolomia binotalis, Cryptophiebia leucotret4 Cydalimaperspeclalis, Cydia spp., T)iaphaniaperspectalLc, Diatraea spp., T)paropsLc cackmnea, Eariac spp., Eldana saccharina, Ephesfia spp., Epinofia spp., Estigmene acrea, Etiella zinckimlla Eucosma spp., Eupoecilia ambiguellq, Euproctis spp., Euxoa spp., Felt/a jacul jferi4 Grapholila spp., iledya nub4feranq, Heliothis spp., Hellula unthils, Herpetogramma spp., Hyphanlria cunea, Keferia lycvpersicella Lasmopalpus lignosellus, Leucvptera scitella Lithocollethis spp., Lobes/a bolran4 Loxoslege bjjIdalis, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra bratcicae, Manduca sexta Mythimna spp., Noctua spp., Operophtera spp., Orniodes indicq, Ostrinia mthilalLç Pammene spp., Pandemtc spp., Panolicfiammeq, Fapaipema nebris, Pectinophora gossypiela, Perileucoptera coffeella Pseudaletia un4iuncta, Phthorimaea opercuiella, Pier/s rapae, Pier/s spp., Plutella xylostel(a, Prays spp., Pseudoplusia spp., Rack/plus/a m Rich/a aThicosta Scirpophaga spp., Sesasnia spp., Sparganothis spp., Spodoplera spp., Sylepta derogate, Synanthedon spp., Thaumetopoea spp., Tortrix spp., lHchoplusia ni, Tuta ahcoluta, and Yponomeuta spp.; from the order Mallophaga, for example, J)amalinea spp., and Trichodectes spp.; from the order Orihoptera, for example, J3latta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Neocurtilla hexadactylq, Periplaneta spp.,, Scapteriscus spp., and SchLctocerca spp.; from the order Psocoptera, for example, Liposce ifs spp.; from the order Siphonaptera, for example, CeratophyThis spp., Ctenocephaiides spp., and Xenopcyiia cheopis; from the order Thysanoplera, for example, Caiiothripsplzaseol4 Frankliniella spp., Heliothrips spp., Here/not/rips spp., Parthenotlsr4n spp., Sciflothnn aurantil, Sericothrips variabilis, Taeniothnps spp., Thnps spp.; -60 -from the order Thysaitura, for example, Lep/sma saccharina.

The active ingredients according to the invention can be used for controlling, i. e. containing or destroying, pests of the abovementioned type which occur in particular on plants, especi- ally on useful phmts and ornamentals in agriculture, in horticulture and in forests, or on or-gans, such as fruits, flowers, foliage, stalks, tubers or roots, of such plants, and in some cases even plant organs which are formed at a later point in time remain protected against these pests. I0

Suitable target crops are, in particular, cereals, such as wheat, barley, we, oats, rice, maize or sorghum; beet, such as sugar or fodder beet; fruit, for example pomaceous fruit, stone fruit or soft fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries or blackberries; leguminous crops, such as beans, lentils, peas or IS soya; oil crops, such as oilseed rape, mustard, poppies, olives, sunflowers, coconut, castor, cocoa or ground nuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants, such as cotton, flax, hemp orjute; citrus fruit, such as oranges, lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes or bell peppers; Lauraceae, such as avocado, Cinnamonium or camphor; and also tobacco, nuts, coffee, eggplants, sugarcane, tea, pepper, grapevines, hops, the plantain family, latex plants and ornamentals.

The invention therefore provides a method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (1), or a composition containing a compound of formula (I), to a pest, a locus of pest, preferably a plant, or to a plant susceptible to attack by a pest, The compounds of formula (I) are preferably used against insects, acarines or nematodes, As for acari, for example, Tetranyc/nis cinnabar/ntis, Tetranychus urticae, Panonychus cliii, Aculops peickassi, Tarsonernus spp..

As for nematodes, for example, Meloidogyne incognita, J3ursapheienchus lignicolus Alarniya ci K4yohara, Aphelenchoides besseyl, Heterodera glycines; Pralylenchus spp..

Additionally, the compounds can be used for controlling animal pests, in particular insects, arachnids, helminths, nematodes and molluscs, which are encountered in agriculture, in horticulture, the field of veterinai'y medicine, in forests, in gardens and leisure facilities, in -61 -the protection of stored products and of materials, and in the hygiene sector. They may preferably be employed as plant protection agents. They may be active against normally sensitive and resistant species and against all or some stages of development.

These pests include inter alia: From the order of the Anoptura (Ph/h/rap/era), for example, Damat/nia spp., l-Iaemalop/nus spp,, Linogna/hus spp., Ped/culus spp,, D/chodec/es spp..

From the class of the Arachnida, for example, Acarus siro, Acer/a sheidoni, Aculops spp., Acutus spp,, Amb/yomina spp., Argas spp,, Jiooph/fns spp., lire v/pa/pus spp,, Bryob/a praeliosa, t7horioptes spp,, Dermany&cns ga/linac, Fo/etranychus spp., Epifriments pyri, to Eute/ranychus spp,, Eriophyes spp,, Hemi/arsonemus spp,, i-iyaiomma spp,, hot/es spp., Latrodectus macians, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyf/ocop/ruta ote/vora, Pofyphagotarsonem its la/us, Psoroptes spp., Rhip/cepha/us spp., Rhizog/yphus spp,, Sarcop/es spp., Scorpio maunis, Sieno/arsonemus spp., Tarsonemus spp,, Te/ranychus spp,, 1/cisafes tycopers/c/.

is From the class of the B/va/va, for example, Drets'sena spp..

From the order of the Chi/opoda, for example, Geophilus spp., Scu/igera spp..

From the order of the Co/cop/era, for example, Acanthosceha'es oh/cents, Adore/its spp., Age/as/ica a/ni, Agriotes spp., Amphima/lon so/ic/i/ia/is, Anohiurnpunctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apogonia spp., Atomaria spp., A//agenus spp,, Bruch/dius oh/cc/us, Bruchus spp,, Ceuihorhynchns spp., C/eonns mend/ct's, Conoderns spp,, Cosmopolites spp., Coslely/ra zealand/ca, Curculio spp., Ciyptorhynchus lapcahi, Dermes/es spp., Diabrolica spp., Epi/achna spp,, Fans/inns cnhae, Gib h/nm psj;lloides, Heteronychus ara/or, Hyiamorpha elegans, Hylotrupes bafitius, Hypera post/ca, J-Jypothenemus spp., Lachnos/erna consanguinea, Lepi/notarsa decem/inea/a, Lissorhop/rns oryzophi/us, Lixus spp., Lyctus spp., Aleligethes aeneus, IVelo/ontha meio/ontha, lvii gdoius spp., lt'ionochamus spp., iVaupaclus xan/hographus, ZWptus holo/eucus, O;yctes rhinoceros, Oiyzaephi/us surinamensis, Ot iorrhynchus sn/ca/us, Oxycetoniajucunda, Phaedon cochleariae, Phy//ophaga spp., Pop/il/a japonica, Premno/rypes spp., Psylliodes chrysocephata, P/inns spp., Rhizobins ventrci//s, Rhizopertha domin/ca, Sitoph/Ins spp., Sphenophorus spp,, S/ernechus spp,, Symphy/eies spp., lenebno mo//for, Jr/ho! ium spp,, irogoderma spp., J}th/ns spp., Xyto/rechns spp,, Zabrus spp., From the order of the Co/lembola, for example, Onychiurus armatus, From the order of the Dciii aptera. for example, Foijicu/a auricnlaria.

From the order of the Dt/opoda, for example, B/an/n/us gui/u/a/us.

-62 -From the order of the 1)/p/era, for example, Act/es spp,, Anopheles spp., B/b/o hor/ulanus, Ca1iehora ery/hrocephala, Cercel//is capt/a/ce, Chrysorny/a spp., Cochi/orny/a spp., Cordyloh/a anthropophaga, Cider spp., Cu/crc bra spp., Dacus oleae, Denna/ohia horn/nA', Drosophila spp., Faint/a spp., Gastroph//us spp., Hyiernyia spp., Hyppobosca spp., Ilypoderma spp., Liriornyza spp., Inc/i/a spp., Musca spp., Nezara spp., Oes/rus spp., Oscine/la fr/I, Pegornyla hyoscyarni, Phorbia spp., Slonioxys spp., ibbanus spp., Janet/a spp., Tipula paludosa, Wohlthhrtia spp..

From the class of the Gas/ropoda, for example, Ar/on spp., B/onipha/ar/a spp., Bit/inns spp., Deroceras spp., Gaiha spp., Lyrnnaea spp., Onconielania spp., Succinea spp.

to From the class of the heirninths, for example, A ncylostoma duodenale, A ncylos/orna ceyian/curn, Acylostorna braz/i/ens/s, Ancy/ostorna spp., A scar/s lubrico/des, A scar/s spp., Brugia;naiay/, I/rug/a I/rnor/, Bunostornurn spp, Chabertia spp, Clonorch/s spp., Cooper/a spp., D/crocoe i/tin, spp., D/clyocauius fl/ar/a, Diphyi/oboihr/urn ia/urn, Dracuncu his n,edinens/s, Ech/nococcus grarnelosus, Ech/nococcus muili/ocularis, Enlerob/us IS verrn/cularLc, Fac/ola spp., J-Taenionchus spp., Heterak/s spp., Hyrnenolepis nana, Hyostronguius spp., Loa Loa, Neinatod/rus spp -, Oesophagostornurn spp -, Op/sthorchis spp., Onchocerca volvuius, Ostertagia spp., Paragon/nuts spp., Sch/stosomen spp., Strongyloicles J'uellehorni, Strongyloides stercoralis, Stronylo/des spp., Taenia sag/na/a, Taenia so//urn, Tr/chineila 5p/rai/s, Trich/neila nat/va, Tr/ch/ne I/a bri/ovi, Tr/chine/ia nelson/, Trich/neila pseudopsira//s, i?ichos/rongu his spp., Th/chur/s tr/chur/a, !Vucherer/a bancro/l/.

It may be furthermore possible to control protozoa, such as E/rner/a.

From the order of the He/crop/era, for example, Anasa iris/is, An/es/lops/s spp., Bl/ssus spp., (alocor/s spp., Carnpy/otnrna l/v/da, (ave/er/us spp., (/,nex spp., (re out/at/es d/hetus, Dasytues pijeris, Dicheiops/iercatus, D/conocor/s hewetti, Dysdercus spp,, l?usch/stus spp., Eurygaster spp., Hel/opeitA' spp., Horc/as nohilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Iviacropes ercavatus, lvf/r/dae, 7\Tezara spp,, Oehalus spp., Pen/omit/tee, Piesma quadrata, P/ezodorees spp., Psalms' ser/atus, Pseudacysta lJE'c Rhodnius spp., Sahihergella singuiar/s, Scoilnophora spp., Stephanitis nash/, T/hraca spp., Tr/atorna spp. -From the order of the Hornop/era, for example, Acyr/hoseon spp., Aeneolarnia spp., Agonoscena spp,, Aleurodes spp., Aieurolobus barodens/s, Aieurolhr/xus spp,, Arnrasca spp,, Anuraph/s cart/ui, A onid/elia spp,, Aphanas't/grna p/ri, Aphis spp., Arhor/d/a apicai/s, Asp/die/la spp., A5p/d/otus spp., Atanus spp., Aulacorthurn solan/, Bern/s/a spp., Brachycandus hei/chiys/i, Brachycoius spp., I/re vicocyne b,'ass'icae, Ca/iigypona inarg/na/a, -63 -Carneocephaiafidg/da, Cerafovacuna lan/gera, Cercopidae, Ceropiastes spp,, Chaelosiphonfrcigaefolii, Ch/onaspis tegalei.'s/s, C/i/or/Ia onuk//, Chrornaph/sjugiand/coia, Chrysomphalusficus, (icadu/ina mhi/ci, Coccomyti/us ha//i, Coccus wp, lryptom}'zus riMs, Dalbulus spp., Dia/eurodes spp., Diaphorina spp., Diaspis spp., Dora/is spp., Drosicha spp., Dysap/i/s spp,, Dysni/coccus spp,, Enipoasca spp., Fr/osoma spp,, Fry fhroneura spp., Fuscel/s b/Iobatus, Geococcus cof/eae, 1-lomalodisca coagulata, Ilyalop ferns arund/n/s, Jcetya spp., Idiocerus spp., Id/oscopus spp., Laodelphar s/hate//us, Lecanium spp., Lep/dosaphes spp., L/paph/s erys/rn/, Macros/phwn spp., Mahanarva/imbr/olala, Itle/anap his sacchari, Aletca/ftel/a spp,, Ale topolophiurn d/rhoc/urn, Alone//ia costa/is, to Mone///opsis pecan/s. Alyzus spp,, ATasono via ribisn/gr/, ATepho fe/fix spp,, AT//apar va/a lugens, Oncornetopia spp., Ortheziapraeionga, Parabemisia myricac, Paratrioza spp., Pariatorla spp, Peniphigus spp, J'eregr/nus ma/d/s, Phenacoccus spp, Phi oeomyzus passerin, Phorodon hurnnh, Phy/loxera spp,, P/nnaspLs as pidisfrae, P/ar ococcus spp., Protopul v/nor/a pyr4form/s, Psendaulacasp/s peniagona, Pseudococcns spp., Psy/la spp., IS Pteromahis spp., Pyri//a spp., Quadrctspidiotus spp., Quesada gigas, /?actrococcus spp., Rhopa/osi/min spp., Saissetia spp., Scaphoides titanus, Schizaphis graminuin, Seienaspidus articulatus, Sogata spp,, Sogate//afiircifèra, Sogatodes spp., Stictocephalafestina, Tena/cqphara malayensis, Tinoca/lis caiyaefo/iae, Tornacpis spp., Toxoptera spp,, Tr/a/eurodes vaporar/orum, T rioza spp., ]jph/ocyba spp., Unaspis spp., Viteus vi/ijb//i.

From the order of the Hyrnenoplera, for example, 1)/pr/on spp., Hoplocampa spp,, Las/us spp,, Alono-rnorium pharaonis, Vespa spp,.

From the order of the [sopoda, for example, Ar,nadi///diuin vu/gare, On/scits asellus, Porcellio scaber.

From the order of the [sop/era, for example, Re//cu/hermes spp., Odon/ofermes spp..

From the order of the Lepidoptera, for example, Acron/cta mcq/o; Aedia Ieuco,nelav, Agrot/s spp,, Alabama argillacea, Ant/cars/a spp,, Barathra brassicae, Buccu/atrix thurberie//a, Bupa/us piniarius, Cacoecia podana, Capita reticu/ana, (i'aipocapsapomone//a, (7ieimatobia brumata, (h/b spp., Chor/stoneurafthnifèrana, (/;sia amb/gue/la, Cnaphaiocerus spp,, Far/as /nsulana, Lu/iesl/a kuehn/eila, Fuproci/s chrysorrhoea, Fuxoa spp,, Fe/I/a spp., Ga//er/a mci/one/ia, He//coverpa spp,, Hello/h/s spp., J-Jofinannophi/a pseudosprete/la, Homona Inagnanima, 1-Jyponomeuta pade I/a, Laphygma spp., L/thoco//etis b/ancardei/a, Lithophane antennata, Loxagrot/s a/b/costa, Lyman/na spp., Itia/acosoma neusir/a, Mamesira brass/cae, Moc/s repanda, ItJylhunna separata, Or/a spp,, -64 -Oulema oryzae, Panol/s flammea, Peci/nophora gossypiella, Phy/locnistis c/ire flu, Pier/s spp., Phi/ella xyf os/ella, Prodenia spp., Pseudale f/a spp,, Pseudop/usia inchidens, Pyrausfa nub/la/is, ASpodoptera spp., Thermesia gemmatalis, Tinea pc/lionel/a, Ti;zeola hissel/le/la, Toririx viridana, Trichopiusia spp -.

From the order of the Or/hop/era, for example, Ache/a domest/cus, B/al/a onenla/es, B/a//el/a german/ca, Cry/lola/pa spp,, Leucophaea maderae, Locus/a spp., Melanoplus spp., Pertianeta americana, Schis/ocerca gregaria.

From the order of the Siphonap/era, for example, Cera/ophy/lus spp,, Xenopsy/la cheopis.

to From the order of the Symphyla, /br example, Scu/igerella inimacu/ala.

From the order of the Thysanopterci, for example, Baliothris bijbrmis, Enneothrrps Jlavens, Hank/in/ella spp., Heliothris spp., Herc/nothr is femoralis, Kakofhriim' spp., Rh/piphorothr/ps cruei;ia/us, Sc/rio/hr/ps spp., Taenioihr/ps cardamoni, Thrips spp, From the order of the Thysanura, for example, Lepisma saccharina, is The phytoparasitic nematodes include, for example, Anguina spp., Aphelenchoides spp., Be/onoaimus spp., Bursaphe/enchus spp., Di/ylenchus d4psaci, Globodera spp., Heliocoty'lenchus spp., 1-leterodera spp., Longiclorus spp,, Meloiclogyne spp,, Pratylenchus spp., ]?adopholus s/mi/is, Ro/ylenchus spp., Trichodorus spp., Tylenchorhynchus spp., i);/enchulus spp., ]j;/enchu/us semienetraus, Xihineina spp..

Furthermore, in the field of veterinary medicine, the novel compounds of the present invention can be effectively used against various harmful animal parasitic pests (endoparasites and ectoparasites), for example, insects and helminthes.

Examples of such animal parasitic pests include the pests as described below.

Examples of the insects include Gasterophilus spp., Stoma'çys spp., Trichodectes spp., J?hodnius spp., Ctenocepha/ides ca/its, C/nrc lecturius, C/enocepha/ic/esjè/is, Lucilia duprina, and the like.

Examples of acari include Ornithodoros spp., Lvodes spp., Boophilus spp., and the like.

In the veterinary fields, e.g. in the field of veterinary medicine, the active compounds according to the present invention are active against animal parasites, in particular ectoparasites or endoparasites, The term endoparasites includes in particular helminths, such as cestodes, nematodes or trematodes, and protozoae, such as coccidia.

-65 -Ectoparasites are typically and preferably arthropods, in particular insects such as flies (stinging and licking), parasitic fly larvae, lice, hair lice, bird lice, fleas and the like; or acarids, such as ticks, for examples hard ticks or soft ticks, or mites, such as scab mites, harvest mites, bird mites and the like.

These parasites include: From the order of the Anopiurida, for example Haeniatopinus spp., Linognathus spp., Pet//cu/us spp., Phtirus spp., Solenopotes spp.; particular examples are: Linognathus setosus, Linognathus v/lull, Linogna/hus or/i/us; Linognallius oi'e,fbrni,s, Linogna/hus pet/a/is, Linognathus stenopsis, Haematopinus as/ni macrocepha/us, J-Jaematopinus to eurysternus, Haemaiopinus suis, Pediculus humanus cap//is, Pediculus human us corporis, Phylloera vastairix, Phthirus pubis, Solenopotes capillatus; from the order oft/ic Mat iop hag/dc: and the suborders Amblycerina and Ischnocerina, /br example inmenopon spp., IVienopon spp., Trinoton spp., Boy/cola spp., Werneckiella spp., Lepiken/ron spp., Damalina spp., Trichodecles spp., Fe//cola spp.; particular examples are: Boy/cola boris, IS Boy/cola ovis, Bovicola urn hata, Darna/ina hovi.s Trichodectes canis, Eel/cola suhrostratus, Bovicola caprae, Lepikentron ovis, Werneckiella equi; from the order oft/ic Ditera and the suhorders Nernatocerina and Brachycerina, fir example A ct/es spp., A nap/ic/es spp., Cuter spp., Simulium spp., Eusimulium spp., Phiehotomus spp., Lutzornyia spp., Cuilcoides spp., Chtysops spp., Odagmnia spp., Wilhelm/a spp., Hybomitra spp., Atylotus spp., Tabanus spp., Ilaematopolci spp., I'hiiiponiyia spp., Bruit/a spp., Musca spp., I-Iydro/aea spp., Slomoxys' spp., Haematohia spp., A'forellia spp., Eannia spp., Gloss/na spp., Call/phora spp., Lucilia spp., Chrysomyla spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., !-Typodermna spp., (;asterophilus spp., Hipobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp.; particular examples are: Act/es aegypli, Aedes alhopictus; A ct/es taeniorhynchus, Anopheles gain b/ac, Anopheles macu/ipennis, (ai/iphora emythrocephaia, Chrysozonap/uvialis, Cu/er quinquefrisciatus, Cu/er pipiens, Cu/er tarsalis, Eannia canicularis, Sarcophcegce caruceria, Stornoxys' ca/c itrcens, I i/in/a paludosce, Luc il/c: cuprinci, Lucilia sericata, S/mu/him reptans, Phiehotorn its papatasi, Phlehotomus longialpis, (*/aginia ornata, Wi/helmia equina, Boophthora erythrocephala, T abanus bronnus, Tabanus 30.spodopterus; I'abanus' airalus; I'abanus sudet/cus, Hybomifra c/urea, Chrysops' cacculiens; Chrysops relic/us; Haemcitopota plu via/is', Haernatopota i/al/ca, I%ius'ca ait/umnalLs', Iviusca domestica, Haematohia irritans irritans, Haematohia irritans erigua, J-!aernatohia stimulans, Hydrotaea irritans, Hydroictea aibiunctct, Ch:ysomnya ch/oropyga, C/it ysornya bezziana, Oestrus ores, Ilypodernia boris, H;podem'mna linea/urn, l'rzherals*iana s/knits, Derniatobia -66 -honititis, Melophagiis ovtniis, Lipoplena capreoli, Lipoplena cervi, Ileppobosta var/egala, Hippobosca eq/i/na, Gaslerophifus inleslinalis, Gasteroph/lus haernorro/daf/s, Gasleroph/lus inermis, Gasterophi/us nasa/is, Gasteropliilus nigricornis, Gasterophilus pecorum, Bra//ia coeca; from the order of the Sihonapterida, fbr example Pulex spp., (tenocephalides spp., 1 inga spp., Xenopsylia spp,, Ceratophyf Ins spp.; part/cit/ar examples are: Clenocephaf ides car/is, Clenocepha f/des/c/is; Pulex Err/tans, I trga per/c tratis, Xenopsyifa cheopis; from the order of the Heteropierida, fbi' example (imex spp., Triatoma spp., Rhodnius spp., Panstrong,,ylus spp From the order of the Biattarida, for example Blatta or/enta/is, Per/planeta to an/er/cat/cl, B/alicia german/ca, Siipe//a spp., (e.g. Suppe 1/a long/palpa); From the subclass of the Acari (A car/na) and the orders of the Meter-and Mesost/gmata, for example Argas spp., Orn/thodorus spp., Otob/us spp., ixodes spp., Amblyomma spp., Rh/p/cephahts' (Boophihts) spp., L)ermacentor spp., Haemophysal/s spp., Hyalon/ma spp., Dermanyss/ts spp., Rh/p/cephalus spp,, (the original genus of multi host IS ticks) Ornithonyssus spp., Pneumonyssus spp., Rail/let/a spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.; particular examples are: Argas persicus, Argas reflex/Is, Ornithodorus mouhata, Otohius megnini, Rhpicephalus (BoophHu) nncroplus, Rhipicephalus (Boophihis) decoloratus, Rhipicephalus (Boophi/us) annulat/Is, Rhi/cepha/us (Boophilus,) caiceratus, JTlyalomma anatoi/cu/n, I-Iya/omma aegypticum, Ilyalomma marg/natum, Hyalomma trans/ens, Rhip/cephalus e i'erts/, ixodes ric/nus, Ixodes hexagon/Is, [codes can/s//ga, [codes pilosus, Ixodes ruhic/Indus, [codes scapular/s. ivodes holocyc//Is; Tfaemaphysaiis concinna, JJaemaphysalis punctala, !-!aemaphysal/s cinnabar/I/a, Haemaphysaiis otophila, Haemaphysa/is /eachi, Haemaphysaiis longicorni, Dermacentor marginatiis, [)ermacei/ior ret/cular/Is, [)ern/acentor pictus, Dermacen/or aIhiviclus, Dermacentor anderconi, Dermacentor variahi/is, J-/ya/omma mauritan/cum, Rhipicepha/us sanguine/is, Rh/icepha/us hursa, Rh/icepha/us appendicu/atus, Rhipicephalus capensis, Rhipicephalus turanicus, Rhipicephalus zainbeziensis, Amblyomma americanum, Amblyomma variegatum, A mhlyomma macu/at/tm, A mhlyomma hehraeum, A mhlyomma cajennense, Dermanyssus ga/li//ac, Ornithonyssus bursa, Ornithonyssus s lviarum, Varroa jacobsoni; from the order of the Aci/ned/da (Prost/gma/a,) andAcaridida (A stigma/a,), for exan/ple Acarap/s spp,, C/icy/el/ella spp,, On ithocheyf el/a spp., Myob/a spp., Psorergales spp., Demodex spp., Trombicula spp., L/strophor/Is spp., A car/Is spp., Tyrophagus spp., (aloglyphus spp., Hypodectes spp., Ptero/ichus spp., Psoropies spp., (horioples spp., Otodectes spp., Sarcoptes spp., Noloedres spp., Knemidocoptes spp., Cytod/tes spp., -67 -Laminosioptes spp,; particular examples are: Cheyietieilayasgur/, Cheyletiefia biakel, Demodex can/sc Demodex boris; Demodex ovis; Dernodex caprae, Demodex equl, Demodex cabal/i, Demodex suis, I"Jeotrom h/cu/a autumna/is, 7'/eotromhicuia desa/eri, 7"Teoschongastia xerothermobia, Troin b/cu/a a/wrnushi, Otodectes cynotis, Notoedres cati, Sarcoptis cat/is, Sarcoptes boris, Sarcoptes ovis; Sarcoptes rup/caprae (S. caprae), Sarcoptes eqid, Sarcoptes sins, Psoroples oi'Ls; Psoroples curt/cull, Psoroptes eq/u, Chor/optes boris, Psoergates mis, Pneumonyssoidic inalige, Pneumonyssoides caninum, Acarapis woodi.

The active compounds according to the invention are also suitable for controlling arthropods, helminths and protozoae, which attack animals.

to Animals include agricultural livestock such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, cultured fish, honeybees.

Moreover, animals include domestic animals -also referred to as companion animals -such as, for example, dogs, cats, cage birds, aquarium fish and what are known as IS experimental animals such as, for example, hamsters, guinea pigs, rats and mice.

By controlling these arthropods, helminths and/or protozoae, it is intended to reduce deaths and improve performance (in the case of meat, milk, wool, hides, eggs, honey and the like) and health of the host animal, so that more economical and simpler animal keeping is made possible by the use of the active compounds according to the invention.

For example, it may be desirable to prevent or interrupt the uptake of blood by the parasites from the hosts.

Also, controlling the parasites may help to prevent the transmittance of infectious agents.

The term "controlling" as used herein with regard to the veterinary field, means that the active compounds are effective in reducing the incidence of the respective parasite in an animal infected with such parasites to innocuous levels.

More specifically, "controlling", as used herein, means that the active compound is effective in killing the respective parasite, inhibiting its growth, or inhibiting its proliferation.

Generally, when used for the treatment of animals the active compounds according to the invention can be applied directly.

Preferably they are applied as pharmaceutical compositions which may contain pharmaceutically acceptable excipients and/or auxiliaries which are known in the art, In the veterinary field and in animal keeping, the active compounds are applied (e.g. administered) in the known manner by enteral administration in the form of; for example, -68 -tablets, capsules, drinks, drenches, granules, pastes, boluses, the feed-through method, suppositories; by parenteral administration, such as, for example, by injections (intramuscular, subcutaneous, intravenous, intraperitoneal and the like), implants, by nasal application, by dermal application in the form of for example, bathing or dipping, spraying, pouring-on and spofting-on, washing, dusting, and with the aid of active-compound-comprising shaped articles such as collars, ear tags, tail tags, limb bands, halters, marking devices and the like.

The active compounds may be formulated as shampoo or as suitable formulations usable in aerosols, unpressurized sprays, for example pump sprays and atomizer sprays.

to When used for livestock, poultry, domestic animals and the like, the active compounds according to the invention can be applied as formulations (for example powders, wettable powders ["WP"], emulsions, emulsifiable concentrates ["EC"], tiowables, homogeneous solutions, and suspension concentrates ["SC"]) which comprise the active compounds in an amount of from Ito 80 percent by weight, either directly or after dilution IS (e.g. 100-to 10 000-fold dilution), or else as a chemical bath.

When used in the veterinary field the active compounds according to the invention may be used in combination with suitable synergists or other active compounds, such as for example, acaricides, insecticides, anthelmintics, anti-protozoal drugs.

In the present invention, a substance having an insecticidal action against pests including all of these is referred to as an insecticide.

An active compound of the present invention can be prepared in conventional formulation forms, when used as an insecticide.

Examples of the formulation forms include solutions, emulsions, wettable powders, water dispersible granules, suspensions, powders, foams, pastes, tablets, granules, aerosols, active compound-infiltrated natural and synthetic materials, microcapsules, seed coating agents, formulations used with a combustion apparatus (for example, fumigation and smoking cartridges, cans, coils or the like as the combustion apparatus), liLY (cold mist, warm mist), and the like.

These formulations can be produced by methods that are known per se.

For example, a formulation can be produced by mixing the active compound with a developer, that is, a liquid diluent or carrier; a liquefied gas diluent or carrier; a solid diluent or carrier, and optionally with a surfactant, that is, an emulsifier and/or dispersant and/or foaming agent.

-69 -in the case where water is used as the developer, for example, an organic solvent can also be used as an auxiliary solvent.

Examples of the liquid diluent or carrier include aromatic hydrocarbons (for example, xylene, toluene, alkylnaphthalene and the like), chlorinated aromatic or chlorinated aliphatic hydrocarbons (for example, chlorobenzenes, ethylene chlorides, methylene chlorides), aliphatic hydrocarbons (for example, cyclohexanes), paraffins (for example, mineral oil fractions), alcohols (for example, butanol, glycols and their ethers, esters and the like), ketones (for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and the like), strongly polar solvents (for example, dimethylformamide, to dimethylsulfoxide and the like), water and the like. The liquefied gas diluent or carrier may be those which are gaseous at normal temperature and normal pressure, for example, aerosol propellants such as butane, propane, nitrogen gas, carbon dioxide and halogenated hydrocarbons. Examples of the solid diluent include pulverized natural minerals (for example, kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, diatomaceous earth, IS and the like), pulverized synthetic minerals (for example, highly dispersed silicic acid, alumina, silicates and the like), and the like. Examples of the solid carrier for granules include pulverized and screened rocks (for example, calcite, marble, pumice, sepiolite, dolomite and the like), synthetic granules of inorganic and organic powder, fine particles of organic materials (for example, sawdust, coconut shells, maize cobs, tobacco stalk and the like), and the like. Examples of the emulsifier and/or foaming agent include nonionic and anionic emulsifiers [for example, polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (for example, alkylaryl polyglycol ether), alkylsulfonates, alkylsulfates, arvlsulfonates and the like], albumin hydro lyzate, and the like. Examples of the dispersant include lignin sulfite waste liquor and methylcellulose, Fixing agents can also be used in the formulations (powders, granules, emulsions), and examples of the fixing agent include carboxymethylcellulose, natural and synthetic polymers (for example, gum arabic, polyvinyl alcohol, polyvinyl acetate, and the like) and the like. Colorants can also be used, and examples of the colorants include inorganic pigments (for example, iron oxide, titanium oxide, Pmssian Blue and the like), organic dyes such as alizarin dyes, a.zo dyes or metal phthalocyanine dyes, and in addition, trace elements such as the salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc, The formulations in general can contain the active ingredient in an amount ranging from 0.1 to 95 percent by weight, and preferably 0.5 to 90 percent> by weight. The compound according to the present invention can also exist as an admixture with other active compounds, for -70 -example, insecticides, poisonous baits, bactericides, miticides, nematicides, fungicides, growth regulators, herbicides and the like, in the form of their commercially useful formulation forms and in the application forms prepared from those formulations.

The content of the compound according to the present invention in a commercially useful application form can be varied within a wide range.

The concentration of the active compound according to the present invention in actual usage can be, for example, in the range of 0.0000001 to 100 percent by weight, and preferably 0.00001 to 1 percent by weight.

The compounds according to the present invention can be used through to conventional methods that are appropriate for the usage form.

The active compound of the present invention have, when used against hygiene pests and pests associated with stored products, stability effective against alkali on lime materials, and also shows excellent residual effectiveness on wood and soil. The compounds of the invention may have favourable properties with respect to amount appled, residue IS formulation, selectivity, toxicity, production methodology, high activity, wide spectrum of control, safety, control of resistant organisms, e.g. pests that are resistant to organic phosphorus agents and/or carbamate agents.

Further embodiments of the invention are described below.

The compounds of formula (I) can be used to combat and control infestations of insect pests such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera, Hymenoptera and Isoptera and also other invertebrate pests, for example, acarine, nematode and mollusc pests. Insects, acarines, nematodes and molluscs are hereinafter collectively referred to as pests. The pests which may be combated and controlled by the use of the invention compounds include those pests associated with agriculture (which term includes the growing of crops for food and fiber products), horticulture and animal husbandry, companion animals, forestry and the storage of products of vegetable origin (such as fruit, grain and timber); those pests associated with the damage of man-made structures and the transmission of diseases of man and animals; and also nuisance pests (such as flies).

The compounds of the invention may be used for example on turf ornamentals, such as flowers, shrubs, broad-leaved trees or evergreens, for example conifers, as well as for tree injection, pest management and the like.

The compounds of the invention may be used to control animal housing pests including: Ants, Bedbugs (adult), Bees, Beetles, Boxelder Bugs, Carpenter Bees, Carpet Beetles, Centipedes, Cigarette, Beetles, Clover Mites, Cockroaches, Confused Flour Beetle, -71 -Crickets, Earwigs, Firebrats, Fleas, Flies, Lesser Grain Borers, Millipedes, Mosquitoes, Red Flour Beetles, Rice Weevils, Saw-toothed Grain Beetles, Silverfish, Sowbugs, Spiders, Termites, Ticks, Wasps, Cockroaches, Crickets, Flies, Litter Beetles (such as Darkling, Hide, and Carrion), Mosquitoes, Pillbugs, Scorpions, Spiders, Spider Mites (Twospotted, Spmce), Ticks.

The compounds of the invention may be used to control ornamental pests including: Ants (Including Imported fire ants), Armyworms, Azalea caterpillars, Aphids, Bagworms, Black vine weevils (adult), Boxelder bugs, Budworms, California oakworms, Cankerworms, Cockroaches, Crickets, Cutworms, Eastern tent caterpillars, Elm leaf beetles, European to sawflies, Fall webworms, Flea beetles, Forest tent caterpillars, Gypsy moth larvae, Japanese beetles (adults), June beefles (adults), Lace bugs, Leaf-feeding caterpillars, Leafhoppers, Leafminers (adults), Leaf rollers, Leaf skeletonizers, Midges, Mosquitoes, Oleander moth larvae, Pillbugs, Pine sawflies, Pine shoot beetles, Pinetip moths, Plant bugs, Root weevils, Sawflies, Scale insects (crawlers), Spiders, Spittlebugs, Striped beetles, Striped oakworms, IS Thrips, Tip moths, Tussock moth larvae, Wasps, Broadmites, Brown softscales, California redscales (crawlers), Clover mites, Mealybugs, Pineneedlescales (crawlers), Spider mites, Whiteflies The compounds of the invention may be used to control turf pests including: Ants (Including Imported fire ants, Armyworms, Centipedes, Crickets, Cutworms, Earwigs, Fleas (adult), Grasshoppers, Japanese beetles (adult), Millipedes, Mites, Mosquitoes (adult), Pillbugs, Sod webworms, Sow bugs, Ticks (including species which transmit Lyme disease), Bluegrass billbugs (adulO, Black turfgrass ataenius (adult), Chiggers, Fleas (adult), Grubs (suppression), Hyperodes weevils (adult), Mole crickets (nymphs and young adults), Mole Crickets (mature adults), Chinch Bugs Examples of pest species which may be controlled by the compounds of formula (1) include: Myzuspers/cae (aphid), Aphis gosypu (aphid), Aphisfitbue (aphid), Lygus spp., (capsids), Dysdercus spp., (capsids), 7'Jilaparvata Ingens (planthopper), 7'/ephotettixc incticeps (leathopper), Nezara spp., (stinkbugs), Eusch/stus spp., (stinkbugs), Leptocor/sa spp,, (stinkbugs), Franklin/ella occidental/s (thrip), Thrips spp., (thrips), kept/no/na dece,nl/neala (Colorado potato beetle), An/honornus grand/s (boll weevil), Aon/diella spp., (scale insects), Trialeurodes spp., (white flies), /3cm/s/a tahaci (white fly), Oswinia izuhilalis (European corn borer), Spodoptera l/ttoralis (cotton leafworm), Hei/oth/s virescens (tobacco budworm), Hei/covetpa armigera (cotton bollworm), I-fe f/coerpa zea (cotton bollworm), -72 -Sy/epia derogafa (cotton leaf roller), Pier/s brasicae (white butterfly), Pin/ella ryios/eiIa (diamond back moth), Agrolis spp., (cutworms), C/i/to suppressv1is (rice stem borer), Locusta_migratoria (locust), Chortlocetes term/nUèra (locust), Diabrotica spp., (rootworms), Panonychus u/mi (European red mite), Panonychus cUrl (citrus red mite), Tetranychus ur/icae (two-spotted spider mite), iètranychus cinnabarinus (carmine spider mite), P/iyitocoplntta oteivora (citrus rust mite), Polyphago/arsoremus ia/irs (broad mite), Brevia/pus spp., (flat mites), Boophll its rn/crop/us (cattle tick), Dermacentor var/abuts (American dog tick), Ctenocephaiides fri/s (cat flea), Liriomyza spp., (leafminer), Musca doniest/ca (housefly), Aedes aegzpt/ (mosquito), Anophe/es spp,, (mosquitoes), Cit/er spp,, to (mosquitoes), Luci/lia spp,, (blowflies), B/a/tel/a german/ca (cockroach), Perip/aneta americana (cockroach), B/a/ta or/entails (cockroach), termites of the Mastotermitidae (for example Mastotermes spp), the Kalotermitidae (for example IYeotennes spp), the Rhinotermitidae (for example Cop/otermes flirmasanus, Re/iculi/ermes /ias'ipes, R. speratu, H i'/rg/n/cus, R. hesperus, and H san/onensis) and the Termitidae (for example Giobi/ermes IS suiireus), So/enopsis geminata (fire ant), Alonomorium pharaonis (pharaoh's ant), Darnailnia spp., and Llno,'nathus spp., (biting and sucking lice), A1e/o/dogyne spp., (root knot nematodes), Glohodera spp., and Heterodera spp., (cyst nematodes), Pra/ytenchus spp., (lesion nematodes), Rhodopholus spp., (banana burrowing nematodes), Ty/enchu/us spp.(citrus nematodes), Haemonchus contortus (barber pole worm), Caenorhabd/Us e/egans.

(vinegar eelworm), i/chosIrongyius spp,, (gastro intestinal nematodes) and Deroceras reticulattim (slug).

The compounds of the invention may be used for pest control on various plants, including soybean (e.g. in some cases 1O-70g/ha), corn (e.g. in some cases 1O-70g/ha), sugarcane (e.g. in some cases 20-200g/ha), alfalfa (e.g. in some cases I O-70g/ha), brassicas (e.g. in some cases I O-50g!ha), oilseed rape (e.g. canola) (e.g. in some cases 20-70g/ha), potatoes (including sweet potatoes) (e.g. in some cases lO-70g/ha), cotton (e.g. in some cases 1O-70g/ha), i-ice (e.g. in some cases 1O-70g/ha), coffee (e.g. in some cases 30-lSOg/ha), citrus (e.g. in some cases 60-200g/ha), almonds (e.g. in some cases 40-I 80g/ha), fruiting vegetables (e.g. tomatoes, pepper, chili, eggplant, cucumber, squash etc.) (e.g. in some cases I0-80g/ha), tea (e.g. in some cases 20-150g/ha), bulb vegetables (e.g. onion, leek etc.) (e.g. in some cases 30-90g/ha), grapes (e.g. in some cases 30-180g/ha), pome fruit (e.g. apples, pears etc.) (e.g. in some cases 30-180g/ha), and stone fruit (e.g. pears, plums etc.) (e.g. in some cases 30-180g/ha).

-73 -The compounds of the invention may be used on soybean to control, for example, Elasinopaipus i/gnoseihis, D/ioboderus abderus, Diabro//ca speciosa, Slerrzechus suhs/gnatus, Form/cit/ac, 4 grot/s yps/Io;z, Juhis spp., Anticarsia gem;natai/s, M'egascelis spp., Procorn/ierrnes spp -, Gryliotalp/dae, Nezara v/nt/u/a, Piezodorus spp -, Acrosternurn spp., IVeornegalolomus spp., Cerolorna /r/fiircafa, Pop/if Ia japon/ca, Edessa spp., Liogenys fliscus, Euchis ins heros, s/a/k borer, Scap/ocorls casfanea, phyliophaga spp., Pseudoplus/a /ncludens, Spoc/optera spp., Bern/s/a tabac/, Agn/otes spp., The compounds of the invention are preferably used on soybean to control D/ioboderus abderus, Diabro f/ca speceosa, Nezara v/n/dula, Piezodorus spp,, Acrosternurn spp,, Cerotorna tni,fiircata, Pop/il/a japon/ca, to Euch/ sins heros, phyllophaga spp,, Agniotes spp..

The compounds of the invention may be used on corn to control, for example, Euchi sins heros, Diche fops /iircatus, Diloboderus abderus, Elasmopalpus fignosef Ins, Spodopierafrug/perda, Nezara i'/n/duia, Cero/oma /nifiircafa, Pop/if Ia japon/ca, Agrof Is ypsilon, Diabro f/ca spec/osa, He/crop/era, Procorn/lermes' ssp., Scaplocor/s casfanea, IS Form/cit/ac, Ju/us ssp., Dalbu his ina/dis, D/ahrotica virgéra, kfoc/s iatzes, Bern/s/a tahaci, he//othis spp., Teiranychus spp., Thris spp., phyliophaga spp., scapioconis spp., Liogenys fuscus, LSocloptera spp,, Os/ritz/a spp., Sesarnia spp,, Agriotes spp.. The compounds of the invention are preferably used on corn to control Euchi s/us heros, D/chelopsfiircatus, D/ioboderus abderus, Nezara vir/dula, (erotorna tniflircafa, Pop/Il/ajapon/ca, Diabro f/ca spec/osa, Diabro f/ca virgifera, lefranychus spp, ihr4os spp, Phyliophaga spp., Scap/ocorls spp., Agr/otes spp.

The compounds of the invention may be used on sugar cane to control, for example, Sheizophorus spp., termites, Mahanarva spp.. The compounds of the invention are preferably used on sugar cane to control termites, Iviahanarva spp,.

The compounds of the invention maybe used on alfalfa to control, for example, J-Jypera hrunneienn/s, J-Jypera post/ca, (ol/as eurytherne, Co/lops spp., Empoasca so/anti, Eoitr/x, Geocor/s spp, Lygus hesperus, Lygus fineofaris, 5v/ss/st/lns spp., %?odoptera spp, Tr/choplus/a n/. The compounds of the invention are preferably used on alfalfa to control h5pera brunneienn/s, Hypera post/ca, Empoasca solana, Ep/ n/i, Lygus hesperus, Lygus ilneofarls, Ji/chopins/a n/.

The compounds of the invention may be used on brassicas to control, for example, Phi/ella xylostelia, P/er/s spp., Iviamestra spp., Phrs/a spp., Trichophisia iii, Phyliotreta spp,, Spodoptera spp., Ernpoasca solana, Thrips spp., Spot/op tera spp., Del/a spp.. The -74 -compounds of the invention are preferably used on brassicas to control Plutella xylostella P/er/s spp,, P/its/a spp,, Trichophisia ru, Phy/loirela spp,, Thrips spp..

The compounds of the invention may be used on oil seed rape, e.g. canola, to control, for example, Mel/gethes spp., (entorhynchus u/api, Psy/loides spp..

The compounds of the invention may be used on potatoes, including sweet potatoes, to control, for example, Lthpoctsca spp., LepI/no/aisa spp., Diabrot/ca spec/osa, Phthor/rnaea spp., Paratrioza spp., Ma/adera unatrida, Agriotes spp.. The compounds of the invention are preferably used on potatoes, including sweet potatoes, to control Empoasca spp,, Lepuinotarsce spp,, Diabro u/ca speciosa, P/'zthorirnaea spp,, Paratr/ozcs spp,, Agriotes to spp..

The compounds of the invention may be used on cotton to control, for example, Anthonornus grand/s, Pec/inophora spp., he/lot/i/s spp., Spodoptera spp., iètranychus spp., Empoasca spp., Dir/ps spp., Bern/s/a tabaci, Lygus spp,, phy/iophaga spp,, Seaptocoris spp., The compounds of the invention are preferably used on cotton to control Anfhonornus IS grand/s. Tetranychus spp., Empoasca spp., ThriØ spp., Lyguts spp., phy//ophaga spp., Scaptocoris spp.

The compounds of the invention may be used on rice to control, for example, Leptocorisa spp,, Cnaphalocros/s spp,, C/i/o spp,, Scirpophaga spp., L/sworhoptrus spp., Oebaluspugnax. The compounds of the invention are preferably used on rice to control Leptocor/sa spp,, Lissorhop/rus spp., Oeba/uspugnax.

The compounds of the invention may be used on coffee to control, for example, J-Jypothenenuts Harnpe/, Per/leucopuera Coffee/Ia, Tetranychus spp,, The compounds of the invention are preferably used on coffee to control Hypothenernus Hampe/, Per/leucoptera Coffee/Ia.

The compounds of the invention may be used on citrus to control, for example, Panonychus cl/ri, Phy//ocopinita oleivora, Brevia/pus spp., Diaphorina c//ri, Sc/ri othr is spp,, Jhrips spp,, Unasp/s spp,, Cerat/t/s cap/ta/a, Phyi/ocn/st/s spp,, The compounds of the invention are preferably used on citrus to control Panonychus c//ri, Phyl/ocopiruta o/e/vora, BreviaIpus spp, Diaphor/na c//ri, Sc/rtothns spp., Thns spp., Phy/loenistis spp.

The compounds of the invention may be used on almonds to control, for example, Aniye/o/s Iran site/ia, Jetraruychus spp.

The compounds of the invention may be used on fruiting vegetable, including tomatoes, pepper, chili, eggplant, cucumber, squash etc, to control Thns spp, Tetranychus spp,, J'oiyphagotarsonernus spp., Acuiops spp,, Enijxxisca spp,, Spodoptera spp., he//a/his -75 -spp., Tn/a absoluta, Liriomyza spp., Bemisia labaci, Trialeurodes spp., Para/rioza spp., Fran/din/ella occiden/alis, Franklin/ella spp., Anthonomus spp., Phylloa!re(a spp., Amrasca spp., Fpilachna spp., Ifalyomorpha spp., Scirtothr/ps spp., inc/nodes spp., Neoleucinodes spp.. The compounds of the invention are preferably used on fruiting vegetable, including tomatoes, pepper, chili, eggplant, cucumber, squash ete, to control, for example, Thrips spp., Thiranyc/na spp., Polyphagolarsonemus spp., Aculops spp., Linpoasca spp., Spodop (era spp., heliothis spp., Tuta absoluta, Liriomyza spp., Paratrioza spp., Franklin/ella occidenlalis, Fran/din/ella spp., Amrasca spp., Scir(othr4os spp., Leucinodes spp., Weoleucinodes spp..

The compounds of the invention may be used on tea to control, for example, Pseudaulacaspis spp., Empoasca spp., Scirtothrzos spp., (aloptilia theivora. The compounds of the invention are prefrerably used on tea to control Empoasca spp., Scirtothrips spp..

The compounds of the invention may be used on bulb vegetables, including onion, leek etc to control, for example, Thrips spp., Spodopa!era spp., heliothis spp.. The compounds of the invention are preferably used on bulb vegetables, including onion, leek etc to control Thrips spp.

The compounds of the invention may be used on grapes to control, for example, J?inpoacca spp., Lobes/a spp., Franklin/ella spp., mr/pc spp., Tetranychus spp., Rbip:$ornthrps Cn.centatus, Ebtetranychus Willamettel, Esythroneura Elegantula, Scaphoides spp.. The compounds of the invention are preferably used on grapes to control Franklin/ella spp., Thrips spp., Thtratwchus spp., Rh/piphornthrips Cruentahtc, Scaphoides spp.

The compounds of the invention may be used on pome fruit, including apples, perars etc, to control, for example, Cacopsylla spp.,Psylla spp., Panonychus ulmi, Cydia pomonella. The compounds of the invention are preferably used on pome fruit, including apples, pears etc, to control Cacopsylla spp., Psylla spp., Panonychus u/mt The compounds of the invention may be used on stone fruit to control, for example, Grapholita molesta, &frtothnps spp., Thripc spp., Franklin/ella spp., Tetranychus spp.. The compounds of the invention are preferably used on stone fhuit to control Scirtothnps spp., 7 hr/ps spp., Franklin/ella spp., Thiranychus spp.The invention therefore provides a method of combating and/or controlling an animal pest, e.g. an invertebrate animal pest, which comprises applying to the pest, to a locus of the pest, or to a plant susceptible to attack by the pest a pesticidally effective amount of a compound of formula (1). In particular, the invention provides a method of combating and/or controlling insects, acarines, nematodes or molluscs -76 -which comprises applying an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or a composition containing a compound of formula (I), to a pest, a locus of pest, preferably a plant, or to a plant susceptible to attack by a pest, The compounds of formula (I) are preferably used against insects, acarines or nematodes, The term "plant" as used herein includes seedlings, bushes and trees. Crops are to be understood as also including those crops which have been rendered tolerant to herbicides or classes of herbicides (e.g. ALS-, GS-, EPSPS-, PPO-and HPPD-inhibitors) by conventional methods of breeding or by genetic engineering. An example of a crop that has been rendered to tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer rape (canola). Examples of crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate-and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® and LibertyLink®.

IS Crops are also to be understood as being those which have been rendered resistant to harmful insects by genetic engineering methods, for example Bt maize (resistant to European corn borer), Bt cotton (resistant to cotton boll weevil) and also Bt potatoes (resistant to Colorado beetle). Examples of Bt maize are the Bt 176 maize hybrids of NK® (Syngenta Seeds). Examples of transgenic plants comprising one or more genes that code for an insecticidal resistance and express one or more toxins are KnockOut® (maize), Yield Gard® (maize), NuCOTI N3 3 B® (cotton), Bollgard® (cotton), NewLeaf® (potatoes), NatureGard® and Protexcta®,Plant crops or seed material thereof can be both resistant to herbicides and, at the same time, resistant to insect feeding ("stacked" transgenic events). For example, seed can have the ability to express an insecticidal Cry3 protein while at the same time being tolerant to glyphosate.

Crops are also to be understood as being those which are obtained by conventional methods of breeding or genetic engineering and contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavor).

In order to apply a compound of formula (I) as an insecticide, acaricide, nematicide or molluscicide to a pest, a locus of pest, or to a plant susceptible to attack by a pest, a compound of formula (I) is usually formulated into a composition which includes, in addition to the compound of formula (I), a suitable inert diluent or carrier and, optionally, a surface active agent (SFA). SFAs are chemicals which are able to modify the properties of an interface (for example, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the -77 -interfacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting). It is preferred that all compositions (both solid and liquid formulations) comprise, by weight, 00001 to 95%, more preferably Ito 85%, for example S to 60%, of a compound of formula (I). The composition is generally used for the control of pests such that a compound of formula (I) is applied at a rate of from 0. Ig toiOkg per hectare, preferably from ig to 6kg per hectare, more preferably from ig to 1kg per hectare.

When used in a seed dressing, a compound of formula (I) is generally used at a rate ofO.000Ig to lOg (for example OOOIg or O.OSg), preferably O.OOSg to lOg, more preferably O.005g to 4g, per kilogram of seed.

to In another aspect the present invention provides a composition comprising a pesticidally effective amount of a compound of formula (I), in particular an insecticida', acaricidal, nematicidal or molluscicidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (1) and a suitable carrier or diluent therefor. The composition is preferably an insecticidal, IS acaricidal, nematicidal or molluscicidal composition.

The compositions can be chosen from a number of formulation types, including dustable powders (DP), soluble powders (SP), water soluble granules (SU), water dispersible granules (WC), wettable powders (WP), granules (CR) (slow or fast release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (IlL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (P0)), micro-emulsions (ME), suspension concentrates (SC), aerosols, fogging/smoke formulations, capsule suspensions (CS) and seed treatment formulations. The formulation type chosen in any instance will depend upon the particular purpose envisaged and the physical, chemical and biological properties of the compound of formula (I), Dustable powders P) maybe prepared by mixing a compound of formula (I) with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montrnorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.

Soluble powders (SP) may be prepared by mixing a compound of formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulfate) or one or more water-soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of -78 -said agents to improve water dispersibility/solubility, The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water soluble granules (SG).

Wettable powders (WP) may be prepared by mixing a compound of formula (I) with one or more solid diluents or carriers, one or more wetting agents and, preferably, one or more dispersing agents and, optionally, one or more suspending agents to facilitate the dispersion in liquids. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water dispersible granules (WG).

Granules (OR) may be formed either by granulating a mixture of a compound of formula (I) and one or more powdered solid diluents or carriers, or from pre-formed blank to granules by absorbing a compound of formula (I) (or a solution thereof in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of formula (I) (or a solution thereof in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulfates or phosphates) and drying if necessary. Agents which are IS commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils). One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent).

Dispersible Concentrates (DC) may be prepared by dissolving a compound of formula (1) in water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a surface active agent (for example to improve water dilution or prevent crystallization in a spray tank).

Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may be prepared by dissolving a compound of formula (T) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents). Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark), ketones (such as cydohexanone or methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), dimethyl amides of fatty acids (such as C-C10 fatty acid dimethylamide) and chlorinated hydrocarbons. An EC product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment. Preparation of -79 -an EW involves obtaining a compound of formula (1) either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in an appropriate solvent) and then emulsiflying the resultant liquid or solution into water containing one or more SFAs, under high shear, to produce an emulsion. Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents which have a low solubility in water.

Microemulsions (ME) may be prepared by mixing water with a blend of one or more solvents with one or more SFAs, to produce spontaneously a thermodynamically stable to isotropic liquid formulation. A compound of formula (I) is present initially in either the water or the solvent/SFA blend. Suitable solvents for use in Ivifis include those hereinbefore described for use in ECs or in EWs. An NilE may be either an oil-in-water or a water-in-oil system (which system is present may be determined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation, An is ME is suitable for dilution into water, either remaining as a microemulsion or forming a conventional oil-in-water emulsion.

Suspension concentrates (SC) may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of formula (I). SCs may be prepared by ball or bead milling the solid compound of formula (I) in a suitable medium, optionally with one or more dispersing agents, to produce a fine particle suspension of the compound. One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle, Alternatively, a compound of formula (I) may be dry milled and added to water, containing agents hereinbefore described, to produce the desired end product.

Aerosol formulations comprise a compound of formula (I) and a suitable propellant (for example n-butane), A compound of formula (I) may also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in non-pressurized, hand-actuated spray pumps.

A compound of formula (I) may be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating, in an enclosed space, a smoke containing the compound, Capsule suspensions (CS) may be prepared in a manner similar to the preparation of EW formulations but with an additional polymerization stage such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a -80 -polymeric shell and contains a compound of formula (I) and, optionally, a carrier or diluent therefor, The polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure. The compositions may provide for controlled release of the compound of formula (I) and they may be used for seed treatment. A compound of formula (I) may also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.

A composition may include one or more additives to improve the biological performance of the composition (for example by improving wefting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of a compound of to formula (I)). Such additives include surface active agents, spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modit the action of a compound of formula (1)).

A compound of formula (1) may also be formulated for use as a seed treatment, for IS example as a powder composition, including a powder for dry seed treatment (DS), a water soluble powder (SS) or a water dispersible powder for slurry treatment (WS), or as a liquid composition, including a tiowable concentrate (FS), a solution (LS) or a capsule suspension (CS). The preparations of DS, SS, WS, PS and LS compositions are very similar to those of, respectively, DP, SP, WP, SC and DC compositions described above. Compositions for treating seed may include an agent for assisting the adhesion of the composition to the seed (for example a mineral oil or a film-forming barrier), Wetting agents, dispersing agents and emulsifying agents may be surface SPAs of the cationic, anionic, amphoteric or non-ionic type.

Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts.

Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulfuric acid (for example sodium lauryl sulfate), salts of sulfonated aromatic compounds (for example sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, butylnaphthalene sulfonate and mixtures of sodium di- /sopropyl-and tri-isopropyl-naphthalene sulfonates), ether sulfates, alcohol ether sulfates (for example sodium laureth-3-sulfate), ether carboxylates (for example sodium laureth-3-carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and -81 -tetraphosphoric acid; additionally these products may be ethoxylated), sulfosuccinamates, paraffin or olefine sulfonates, taurates and lignosulfonates.

Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.

Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (for to example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins.

Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).

is A compound of formula (I) may be applied by any of the known means of applying pesticidal compounds. For example, it may be applied, formulated or unformulated, to the pests or to a locus of the pests (such as a habitat of the pests, or a growing plant liable to infestation by the pests) or to any part of the plant, including the foliage, stems, branches or roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapor or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water-soluble bag) in soil or an aqueous environment.

A compound of formula (1) may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems, Compositions for use as aqueous preparations (aqueous solutions or dispersions) are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being added to water before use. These concentrates, which may include DCs, SCs, ECs, EWs, MEs, SGs, SPs, WPs, WOs and CSs, are often required to withstand storage for prolonged periods and, after such storage, to be capable of addition to water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment. Such aqueous preparations may -82 -contain varying amounts of a compound of formula (1) (for example 0.0001 to 10%, by weight) depending upon the purpose for which they are to be used.

A compound of formula (I) may be used in mixtures with fertilizers (for example nitrogen-, potassium-or phosphorus-containing fertilizers). Suitable formulation types include granules of fertilizer, The mixtures preferably contain up to 25% by weight of the compound of formula (I).

The invention therefore also provides a fertilizer composition comprising a fertilizer and a compound of formula (I).

The compositions of this invention may contain other compounds having biological to activity, for example micronutrients or compounds having fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.

The compound of formula (I) may be the sole active ingredient of the composition or it may be admixed with one or more additional active ingredients such as a pesticide, e,g, a insecticide, fungicide or herbicide, or a synergist or plant growth regulator where appropriate, Is An additional active ingredient may provide a composition having a broader spectrum of activity or increased persistence at a locus; synergize the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the compound of formula (I); or help to overcome or prevent the development of resi stance to individual components. The particular additional active ingredient will depend upon the intended utility of the composition.

The compounds of the invention are also useful in the field of animal health, e.g. they may be used against parasitic invertebrate pests, more preferably against parasitic invertebrate pests in or on an animal. Examples of pests include nematodes, trematodes, cestodes, flies, mites, tricks, lice, fleas, true bugs and maggots. The animal may be a non-human animal, e.g. an animal associated with agriculture, e.g. a cow, a pig, a sheep, a goat, a horse, or a donkey, or a companion animal, e.g. a dog or a cat.

In a further aspect the invention provides a compound of the invention for use in a method of therapeutic treatment, In a further aspect the invention relates to a method of controlling parasitic invertebrate pests in or on an animal comprising administering a pesticidally effective amount of a compound of the invention, The administration may be for example oral administration, parenteral administration or external administration, e.g. to the surface of the animal body. In a further aspect the invention relates to a compound of the invention for controlling parasitic invertebrate pests in or on an animal, In a further aspect the invention -83 -relates to use of a compound of the invention in the manufacture of a medicament for controlling parasitic invertebrate pests in or on an animal In a further aspect, the invention relates to a method of controlling parasitic invertebrate pests comprising administering a pesticidafly effective amount of a compound of the invention to the environment in which an animal resides.

In a further aspect the invention relates to a method of protecting an animal from a parasitic invertebrate pest comprising administering to the animal a pesticidally effective amount of a compound of the invention. In a further aspect the invention relates to a compound of the invention for use in protecting an animal from a parasitic invertebrate pest.

to In a further aspect the invention relates to use of a compound of the invention in the manufacture of a medicament for protecting an animal from a parasitic invertebrate pest.

In a further aspect the invention provides a method of treating an animal suffering from a parasitic invertebrate pest comprising administering to the animal a pesticidally effective amount of a compound of the invention. In a further aspect the invention relates to IS a compound of the invention for use in treating an animal suffering from a parasitic invertebrate pest. In a frirther aspect the invention relates to use of a compound of the invention in the manufacture of a medicament for treating an animal suffering from a parasitic invertebrate pest.

In a further aspect, the invention provides a pharmaceutical composition comprising a compound of the invention and a pharmaceutically suitable excipient.

The compounds of the invention may be used alone or in combination with one or more other biologically active ingredients.

In one aspect the invention provides a combination product comprising a pesticidally effective amount of a component A and a pesticidally effective amount of component B wherein component A is a compound of the invention and component B is a compound as described below.

The compounds of the invention may be used in combination with anthelmintic agents. Such anthelmintic agents include, compounds selected from the macrocyclic lactone class of compounds such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin derivatives as described in EP-357460, EP-444964 and EP-59429i, Additional anthelmintic agents include semisynthetic and biosynthetic avermectin/milbemycin derivatives such as those described in US-50l5630, WO-94l5944 and WO-9522552. Additional anthelmintic agents indude the benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole, -84 -mebendazole, oxfendazole, oxibendazole, parbendazole, and other members of the class.

Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel, Additional anthelmintic agents include flukicides, such as triclabendazole and clorsulon and the cestocides, such as praziquantel and epsiprantel.

The compounds of the invention may be used in combination with derivatives and analogues of the paraherquamide/marcfortine class of anth&mintic agents, as well as the antiparasitic oxazolines such as those disclosed in US-5478855, Us-4639771 and DE-19520936.

to The compounds of the invention may be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents as described in WO- 96t5121 and also with anthelmintic active cyclic depsipeptides such as those described in WO-9611945, WO-9319053, WO-9325543, EP-626375, EP-382173, WO-9419334, EP- 382173, and EP-503538, is The compounds of the invention may be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and the like.

The compounds of the invention may be used in combination with terpene alkaloids, for example those described in International Patent Application Publication Numbers W095!19363 or W004/72086, particularly the compounds disclosed therein.

Other examples of such biologically active compounds that the compounds of the invention may be used in combination with include but are not restricted to the following: Organophosphates: acephate, azam ethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos, chiorethoxyphos, chiorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methyl suiphone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothi on, fenthi on, flupyrazofos, fonofos, fonriothion, fosthiazate, heptenophos, isazophos, isothioate, isoxathion, malathion, methacriphos, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate, phosalone, phosfolan, phosphocarb, phosmet, phosphamidon, phorate, phoxim, pirimiphos, pirimiphos-methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, -85 -pyridapenthion, quinaiphos, suiprophos, temephos, terbufos, tebupirimfos. tetrachlorvinphos, thimeton, triazophos, trichiorfon, vamidothion, Carbamates: a] anycarb, a] dicarb, 2-sec-butylphenyl methyl carbamate, benfijracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-rn-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-5 1717.

Pyrethroids: acrinathin, allethrin, aiphametrin, 5-benzyl-3-furylmethyl (E) - (1 R)-cis-2,2-dimethyl-3-(2-oxothio]an-3-y]idenemethyl) cyclopropanecarboxylate, to bifenthrin, beta -cyfluthrin, cyfluthrin, a-cypermethrin, beta -cypermethrin, bioal]ethrin, bioallethrin((S)-cyclopentyli somer), bioresmethrin, bifenthrin, NCI-85 193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, ethofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins IS (natural products), resmethrin, tetramethrin, transfluthrin, theta-cyperniethrin, silafluofen, t-fluvalinate, tefluthrin, tralomethrin, Zeta-cypermethrin.

Arthropod growth regulators: a) chitin synthesis inhibitors: benzoylureas: chl orfluazuron, diflubenzuron, tluazuron, flucycloxuron, f]ufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, chiorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.

Other antiparasitics: acequinocyl, arnitraz, AKD-1022, ANS-1 18, azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl, bromopropylate, BTG-504, BTG- 505, camphechlor, cartap, chlorobenzilate, chiordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine, diacloden, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, ethofenprox, fenazaquin, flumite, MTI-800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox, fluproxyfen, halofenprox, hydramethylnon, 11(1-220, kanemite, NC-196, neem guard, nidinorterfuran, nitenpyram, SD-3 5651, WL-t 08477, pirydaryl, propargite, protrifenbute, pymethrozine, pyridaben, pyrimidifen, NC-t t t 1, R- 195,RH-0345, RH-2485, RYI-210, S-1283, S-]833, SI-860], silafluofen, silomadine, spinosad, tebufenpyrad, tetradifon, tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosyn, trinactin, verbutin, vertalec, YI-53 0 t.

-86 -Fungicides: acibenzolar, aldimorph, ampropylfos, andoprim, azaconazole, azoxystrobin, benalaxyl, benomyl, bialaphos, blasticidin-S, Bordeaux mixture, bromuconazol e, bupirimate, carpropamid, captafol, captan, carbendazim, chl orfenazole, chioroneb, chioropicrin, chiorothalonil, chiozolinate, copper oxychioride, copper salts, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, cyprofuram, RH-7281, diclocymet, diclobutrazole, diclomezine, dicloran, difenoconazole, RP-4072 13, dimethomorph, domoxystrobin, diniconazole, diniconazole-M, dodine, edifenphos, epoxiconazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fencaramid, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fluazinam, fludi oxonil, flumetover, flumorf/flumorlin, fentin to hydroxide, fluoxastrobin, fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fosetyl-aluminium, thralaxyl, furametapyr, hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, krsoxim-methyl, mancozeb, maneb, mefenoxam, mepronil, metalaxyl, metconazole, metominostrobin/fenominostrobin, metrafenone, myclobutanil, neo-asozin, nicobifen, orysastrobin, oxadixyl, penconazole, pencycuron, probenazole, prochloraz, IS propamocarb, propioconazole, proquinazi d, prothi oconazol e, pyrifenox, pyraclostrobi n, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole, tetrconazole, thiabendazole, thifiuzamide, thiophanate-methyl, thiram, tiadinil, thadimefon, thadimenol, tricyclazole, trifloxystrobin, triticonazole, validamycin, vinclozin, Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, virus and fungi.

Bacterici des: chlortetracycline, oxytetracycline, streptomycin, Other biological agents: enrofloxacin, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, denbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, fi orfeni col, busereli n, cefovecin, tul athromycin, ceftiour, carprofen, metaflumizone, praziquarantel, triclabendazole.

When used in combination with other active ingredients, the compounds of the invention are preferably used in combination with the following (where "Tx" means a compound of formula (I), and in particular a compound selected from selected from Table I (compounds 1.1. to 1.75) or Table A (compounds 1 to 7), which may result in a synergistic combination with the given active ingredient): imidacloprid + Tx, enrofloxacin + Tx, praziquantel + Tx, pyrantel embonate + Tx, feb2mtel + Tx, penethamate + Tx, moloxicam + Tx, cefalexin + Tx, kanamycin + Tx, pimobendan + Tx, clenbuterol + Tx, fipronil + Tx, ivermectin + Tx, omeprazole + Tx, tiamulin + Tx, benazepril + Tx, milbemycin + Tx, cyromazine + Tx, thiamethoxam + Tx, pyriprole + Tx, deltamethrin + Tx, cefquinome + Tx, -87 -florfenicol + Tx, buserelin + Tx, cefovecin + Tx, tulathromycin + Tx, ceftiour + Tx, selamectin + Tx, carprofen + Tx, metaflumizone + Tx, moxidectin + Tx, methoprene (including S-methoprene) + Tx, clorsulon + Tx, pyrantel + Tx, amitraz + Tx, triclabendazole + Tx, avermectin + Tx, abamectin + Tx, emamectin + Tx, eprinomectin + Tx, doramectin + Tx, selamectin + Tx, nemadectin + Tx, albendazole + Tx, cambendazole + Tx, fenbendazole + Tx, flubendazole + Tx, mebendazole + Tx, oxfendazole + Tx, oxibendazole + Tx, parbendazole + Tx, tetramisole + Tx, levamisole + Tx, pyrantel pamoate + Tx, oxantel + Tx, morantel + Tx, triclabendazole + Tx, epsipranAel + Tx, fipronil + Tx, lufenuron + Tx, ecdysone + Tx or tebufenozide + Tx; more preferably, enrofloxacin + Tx, praziquantel + Tx, to pyrantel embonate + Tx, febantel + Tx, penethamate + Tx, moloxicam + Tx, cefalexin + Tx, lcanamycin + Tx, pimobendan + Tx, clenbuterol + Tx, omeprazole + Tx, tiamulin + Tx, benazepril + Tx, pyriprole + Tx, cefquinome + Tx, florfenicol + Tx, buserelin + Tx, cefovecin + Tx, tulathromycin + Tx, ceftiour + Tx, selamectin + Tx, carprofen + Tx, moxidectin + Tx, clorsulon + Tx, pyrantel + Tx, eprinomectin + Tx, doramectin + Tx, IS selamectin + Tx, nemadectin + Tx, albendazole + Tx, cambendazole + Tx, fenbendazole + Tx, flubendazole + Tx, mebendazole + Tx, oxfendazole + Tx, oxibendazole + Tx, parbendazole + Tx, tetramisole + Tx, levamisole + Tx, pyrantel pamoate + Tx, oxantel + Tx, morantel + Ix, triclabendazole + Tx, epsiprantel + Tx, lufenuron + Tx or ecdysone + Tx; even more preferably enrofloxacin + Tx, praziquantel + Tx, pyrantel embonate + Tx, febantel + Tx, penethamate + Tx, moloxicam + Tx, cefalexin + Tx, kanamycin + Tx, pimobendan + Tx, clenbuterol + Tx, omeprazole + Tx, tiamulin + Tx, benazepril + Tx, pyriprole + Tx, cefquinome + Ix, florfenicol + Tx, buserelin + Tx, cefovecin + Tx, tulathromycin + Tx, ceftiour + Tx, selamectin + Tx, carprofen + Tx, moxidectin + Tx, clorsulon + Ix or pyrantel + Tx, Examples of ratios include 100:1 to 1:6000, 50:1 to 1:50, 20:1 to 1:20, even more especiallyfrom 10:1 to 1:10, 5:1 to 1:5, 2:1 to 1:2, 4:1 to 2:1, 1:1, ors:1, ors:2, or 5:3, or 5:4, or4:1, or4:2, or4:3, or3:1, or3:2, or2:1, or 1:5, or2:5, or3:5, or4:5, or 1:4, or2:4, or 3:4, or 1:3, or2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or2:35, or4:35, or 1:75, or 2:75, or4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or2:350, or4:350, or 1:750, or 2:750, or 4:750. Those mixing ratios are understood to include, on the one hand, ratios by weight and also, on the other hand, molar ratios.

Of particular note is a combination where the additional active ingredient has a different site of action from the compound of formula I. In certain instances, a combination with at least one other parasitic invertebrate pest control active ingredient having a similar -88 -spectrum of control but a different site of action will be particularly advantageous for resistance management. Thus, a combination product of the invention may comprise a pesticidally effective amount of a compound of formula I and pesticidaHy effective amount of at least one additional parasitic invertebrate pest control active ingredient having a similar spectrum of control but a different site of action, One skilled in the art recognizes that because in the environment and under physiological conditions salts of chemical compounds are in equilibrium with their corresponding non salt forms, salts share the biological utility of the non salt forms.

Thus a wide variety of salts of compounds of the invention (and active ingredients to used in combination with the active ingredients of the invention) may be useful for control of invertebrate pests and animal parasites. Salts include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids, The compounds of the invention also include N-oxides, Accordingly, the IS invention comprises combinations of compounds of the invention including N-oxides and salts thereof and an additional active ingredient including N-oxides and salts thereof The compositions for use in animal health may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants). Such formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thi xotropic thickeners), in-container microbial growth (antimicrobial s), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes. Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes, Examples of formulation auxiliaries and additives include those listed in McCutcheon s Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.

The compounds of the invention can be applied without other adjuvants, but most often application will be of a formulation comprising one or more active ingredients with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use. One method of application involves spraying a water -89 -dispersion or refined oil solution of the combination products. Compositions with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance compound efficacy. Such sprays can be applied from spray containers such as a can, a bottle or other container, either by means of a pump or by releasing it from a pressurized container, e.g., a pressurized aerosol spray can. Such spray compositions can take various forms, for example, sprays, mists, foams, fumes or fog. Such spray compositions thus can further comprise propeflants, foaming agents, etc. as the case may be. Of note is a spray composition comprising a pesticidally effective amount of a compound of the invention and a carrier. One embodiment of such a spray composition to comprises a pesticidally effective amount of a compound of the invention and a propellant.

Representative propellants include, but are not limited to, methane, ethane, propane, butane, isobutane, butene, pentane, isopentane, neopentane, pentene, hydrofluorocarbons, chlorofluorocarbons, dimethyl ether, and mixtures of the foregoing. Of note is a spray composition (and a method utilizing such a spray composition dispensed from a spray IS container) used to control at least one parasitic invertebrate pest selected from the group consisting of mosquitoes, black flies, stable flies, deer flies, horseflies, wasps, yellow jackets, hornets, ticks, spiders, ants, gnats, and the like, including individually or in combinations.

The controlling of animal parasites includes controlling external parasites that are parasitic to the surface of the body of the host animal (e.g., shoulders, armpits, abdomen, inner part of the thighs) and internal parasites that are parasitic to the inside of the body of the host animal (e.g., stomach, intestine, lung, veins, under the skin, lymphatic tissue).

External parasitic or disease transmitting pests include, for example, chiggers, ticks, lice, mosquitoes, flies, mites and fleas, Internal parasites include heartworms, hookworms and helminths. The compounds of the invention may be particularly suitable for combating external parasitic pests. The compounds of the invention may be suitable for systemic and/or non-systemic control of infestation or infection by parasites on animals.

The compounds of the invention may be suitable for combating parasitic invertebrate pests that infest animal subjects including those in the wild, livestock and agricultural working animals, Livestock is the term used to refer (singularly or plurally) to a domesticated animal intentionally reared in an agricultural setting to make produce such as food or fiber, or for its labor; examples of livestock include cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, hens, turkeys, ducks and geese (e.g., raised for meat, milk, bufter, eggs, fur, leather, feathers and/or wool), By combating parasites, fatalities and -90 -performance reduction (in terms of meat, milk, wool, skins, eggs, etc.) are reduced, so that applying the compounds of the invention allows more economic and simple husbandry of animals.

The compounds of the invention may be suitable for combating parasitic invertebrate pests that infest companion animals and pets (e.g., dogs, cats, pet birds and aquarium fish), research and experimental animals (e.g., hamsters, guinea pigs, rats and mice), as well as animals raised for/in zoos, wild habitats and/or circuses.

In an embodiment of this invention, the animal is preferably a vertebrate, and more preferably a mammal, avian or fish, In a particular embodiment, the animal subject is a to mammal (including great apes, such as humans). Other mammalian subjects include primates (e.g., monkeys), bovine (e.g., cattle or dairy cows), porcine (e.g., hogs or pigs), ovine (e.g., goats or sheep), equine (e.g., horses), canine (e.g., dogs), feline (e.g., house cats), camels, deer, donkeys, buffalos, antelopes, rabbits, and rodents (e,g,, guinea pigs, squirrels, rats, mice, gerbils, and hamsters), Avians include Anatidae (swans, ducks and geese), Columbidae IS (e,g,, doves and pigeons), Phasianidae (e,g., partridges, grouse and turkeys), Thesienidae (e.g., domestic chickens), Psittacines (e.g., parakeets, macaws, and parrots), game birds, and ratites (e.g., ostriches), Birds treated or protected by the compounds of the invention can be associated with either commercial or noncommercial aviculture. These include Anatidae, such as swans, geese, and ducks, Columbidae, such as doves and domestic pigeons, Phasianidae, such as partridge, grouse and turkeys, Thesienidae, such as domestic chickens, and Psittacines, such as parakeets, macaws and parrots raised for the pet or collector market, among others, For purposes of the present invention, the term "fish" is understood to include without limitation, the Teleosti grouping of fish, i.e., teleosts, Both the Salmoniformes order (which includes the Salmonidae family) and the Perciformes order (which includes the Centrarchidae family) are contained within the Teleosti grouping, Examples of potential fish recipients include the Salmonidae, Sen'anidae, Sparidae, Cichlidae, and Centrarchidae, among others, Other animals are also contemplated to benefit from the inventive methods, including marsupials (such as kangaroos), reptiles (such as farmed turtles), and other economically important domestic animals for which the inventive methods are safe and effective in treating or preventing parasite infection or infestation, Examples of parasitic invertebrate pests controlled by administering a pesticidally effective amount of the compounds of the invention to an animal to be protected include -91 -ectoparasites (arthropods, acarines, etc.) and endoparasites (helminths, e.g., nematodes, trematodes, cestodes, acanthocephalans, etc.).

The disease or group of diseases described generaHy as helminthiasis is due to infection of an animal host with parasitic worms known as helminths. The term helminths' is meant to include nematodes, trematodes, cestodes and acanthocephalans. Helminthiasis is a prevalent and serious economic problem with domesticated animals such as swine, sheep, horses, cattle, goats, dogs, cats and pouttrv.

Among the helminths, the group of worms described as nematodes causes widespread and at times serious infection in various species of animals.

to Nematodes that are contemplated to be treated by the compounds of the invention include, without limitation, the following genera: Acanthoche//onema, Aelurostrongy/us, Ancyfostoma, Ang/ostrong,yins, Ascaridia, Ascar/s, Brugia, Bunostornurn, (yap/f far/a, Cha bert/ct, Cooper/a, Crenosorna, D/cfyoca;this, Dioctophyrne, Dipetafonerna, D/phyllobofhr/uni, Derojifarea, Dracuncu his, Enlerobeus, E/iaro/des, Haemonchus, IS J-Jeterak/s, Lagochi/ascar/s, Loa, Mànsone 1/a, jtfue//er/us, ATecator, iVematod/rus, ()esophagostornurn, Ostertagia, Oxyur/s, Parq fl/ar/a, Par ascar/s, Physa/optera, Protostrongylus, Setar/a, Sp/rocerca, Stephanofi/aria, Strongylo/des, Strongylus, i/ic/az/a, Toxascar/s, Toxocara, Tr/ch/ne/fa, Tr/chonema, Tr/chosirongy/us, Tr/chur/s, Unc/naria and Wucherer/a.

Of the above, the most common genera of nematodes infecting the animals referred to above are Haernonchus, Tr/chostrongyhis, Ostertag/a, ATernatod/rus, Cooper/a, Ascar/s, Bunostotnum, Oesophagoseornutn, Chahertia, Tr/chur/s, Strongyhis, Trichonema, D/ctyocau/us, (api//ar/a, Heterakis, Toxocara, A scar/c//a, Oxyur/s, Ancylostoma, Uncinar/a, Toxascar/s and Parascar/s. Certain of these, such as ATernatoc/irus, Cooper/a and Oesophagostomum attack primarily the intestinal tract while others, such as J-!aemonchus and Ostertagia, are more prevalent in the stomach while others such as Dictyocan/us are found in the lungs, Still other parasites may be ocated in other tissues such as the heart and blood vessels, subcutaneous and lymphatic tissue and the like.

Trematodes that are contemplated to be treated by the invention and by the inventive methods include, without limitation, the following genera: Afar/a, Pàsciofa, Nanophye Ins, Op/sthorch/s, Paragoninius and Sch/stosorna.

Cestodes that are contemplated to be treated by the invention and by the inventive methods include, without limitation, the following genera: Dihy//obothr/um, Di/yd/u;n, Sp/rornetra and Then/a.

The most common genera of parasites of the gastrointestinal tract of humans are Ancyloslorna, Necalor, Ascaris, Sirongy hides, Trichinella, Capillaria, Trichuris and Fnterobiu& Other medically important genera of parasites which are found in the blood or other tissues and organs outside the gastrointestinal tract are the filarial worms such as Wuchereria, Brugia, Onchocerca and Loa, as well as Dracunculus and extra intestinal stages of the intestinal worms Sirongyloides and Thichinella.

Numerous other helminth genera and species are known to the art, and are also contemplated to be treated by the compounds of the invention. These are enumerated in great detail in Textbook of Veterinary Clinical Parasitology, Volume I, Helminths, E. J. L. Soulsby, F. A. Davis Co., Philadelphia, Pa.; Helminths, Arthropods and Protozoa, (6Edition of Monnig's Veteiinary Helminthology and Entomology), B. J. L. Soulsby, Williams and Wilkins Co., Baltimore, Md.

The compounds of the invention may be effective against a number of animal ectoparasites (e.g., arthropod ectoparasites of mammals and birds).

Insect and acarine pests include, e.g., biting insects such as flies and mosquitoes, mites, ticks, lice, fleas, true bugs, parasitic maggots, and the like.

Adult flies include, e.g., the horn fly or Haernatobia initans, the horse fly or Tahanus spp., the stable fly or Stomoxys calcitrans, the black fly or S/mull urn the deer fly or Chrysops spp., the louse fly orMelophagus ovinus, and the tsetse fly or Gloss/na spp..

Parasitic fly maggots include, e.g., the bot fly (Oestrus ovis and Cuterebra spp.), the blow fly or Phaenicia spp., the screwwoim or Cochliornyia hominivorax, the cattle grub or Hypoderma spp., the fleecewonn and the Gastrophilus of horses. Mosquitoes include, for example, Culex spp., Anopheles spp., and Aedes spp.

Mites include Mesostigmalphalalpha spp., e.g., rnesactigmatidc such as the chicken mite, Dennalphatycsus galphallin.c4pMe; itch or scab mites such as Sarcoptidae spp., for example, Salpharcoptes scaiphabiel; mange mites such as Psoroptidae spp., including Chorioptes boy/s and.Psoroptes ovis; chiggers e.g., 7i'vmbiculidae spp., for example the North American chigger, Trombiculaipha alphajfredthigesi.

Ticks include, e.g., soft-bodied ticks including Argasidae spp., for example Argalphas spp., and Ornilhodoros spp.; hard-bodied ticks including ixoclidAe spp., for example Rh4uicephalphalus sanguineus, Derrnacentor variabilis, Derrnacenlor andersoni, Amblyomma americanism, frocks scapular/s and other iThipicephalus spp., (including the former Boophilus genera).

Lice include, e.g., sucking lice, e.g., Menopon spp..

-93 -and Boy/cola spp.; biting lice, e.g., Haerna/opinns spp., L/nognathus spp., and Solenopo/es spp Fleas include, e.g., (tenocephalides spp., such as dog flea ((tenocephalides can/s) and cat flea (Ctenocephal/destèl/s); Xenopsylia spp., such as oriental rat flea (Xenop5ylia cheop/s); and Pu/er spp., such as human flea (Pu Icr frr/tans).

True bugs include, e.g., C/ni/c/dae or e.g., the common bed bug (C/rnex fec/u/ar/us); Tr/atorninae spp., including triatomid bugs also known as kissing bugs; for example Rhocin/us prolextis and Iria/orna spp.

Generally, flies, fleas, lice, mosquitoes, gnats, mites, ticks and helminths cause to tremendous losses to the livestock and companion animal sectors, Arthropod parasites also are a nuisance to humans and can vector disease-causing organisms in humans and animals.

Numerous other parasitic invertebrate pests are known to the art, and are also contemplated to be treated by the compounds of the invention, These are enumerated in great detail in Medical and Veterinary Entomology, D. S. Kettle, John Wiley AND Sons, New Is York and Toronto; Control of Arthropod Pests of Livestock: A Review of Technology, R. 0.

Dmmmand, S. E. George, and S. E. Kunz, CRC Press, Boca Raton, FIa.

The compounds of the invention may also be effective against ectoparasites including: flies such as J-Jaematobia (Lyperos/cç) fri/tans (horn fly), S/mu//urn spp., (Nackfly), Gloss/na spp., (tsetse flies), Hydrotaea /17/tans (head fly), Musca autumnal/s (face fly), Musca domes//ca (house fly), More/f/a s/nip/er (sweat fly), ithcunts spp., (horse fly), ifypoderma bov/s, J-Jypoderma //neat;ern, Luc/l/a ser/cata, Luc/ila cupr/na (green blowfly), Cal//phora spp., (blowfly), Pro/ophorrn/a spp., Oes/rus ov/s (nasal botfly), (ui/co/des spp., (midges), Hipobosca equ/ne, Gasiroph/lus intest/nalis, Gastroph/ius haenjorrho/dai/s and Gas'/roph/lus nasal/s; lice such as Bar/cola (Damalinia) hov/s, Boy/cola equ/, Haernatop/nus as/in, Eel/cola snhros/ratus, J-l'eterodoxus spin/ger, Lignonathus selosus and Tr/chodectes canEs; keds such as ltfelophagus ovinus; and mites such as Psoroptes spp., Sarcoptes scabei, Chorioptes bov/s, Dernodex equ/, Chey/et/e//a spp., IVotoedres cat/, Trornhicu/a spp., and Otodectes cyanot/s (ear mites).

Treatments of the invention are by conventional means such as by enteral administration in the form of for example, tablets, capsules, drinks, drenching preparations, granulates, pastes, boli, feed-through procedures, or suppositories; or by parenteral administration, such as, for example, by injection (including intramuscular, subcutaneous, intravenous, intraperitoneal) or implants; or by nasal administration.

-94 -When compounds of the invention are applied in combination with an additional biologically active ingredient, they may be administered separately e.g. as separate compositions. In this case, the biologically active ingredients may be administered simultaneously or sequentially. Alternatively, the biologically active ingredients may be components of one composition.

The compounds of the invention may be administered in a controlled release form, for example in subcutaneous or orally adminstered slow release formulations.

Typically a parasiticidal composition according to the present invention comprises a compound of the invention, optionally in combination th an additional biologically active to ingredient, or N-oxides or salts thereof with one or more pharmaceutically or veterinarily acceptable carriers comprising excipients and auxiliaries selected with regard to the intended route of administration (e.g., oral or parenteral administration such as injection) and in accordance with standard practice. In addition, a suitable carrier is selected on the basis of compatibility with the one or more active ingredients in the composition, including such IS considerations as stability relative to pt-I and moisture content. Therefore of note are compounds of the invention for protecting an animal from an invertebrate parasitic pest comprising a parasitically effective amount of a compound of the invention, optionally in combination with an additional biologically active ingredient and at least one carrier.

For parenteral administration including intravenous, intramuscular and subcutaneous injection, the compounds of the invention can be formulated in suspension, solution or emulsion in oily or aqueous vehicles, and may contain adjuncts such as suspending, stabilizing and/or dispersing agents.

The compounds of the invention may also be formulated for bolus inj ection or continuous infusion. Pharmaceutical compositions for injection include aqueous solutions of water-soluble forms of active ingredients (e.g., a salt of an active compound), preferably in physiologically compatible buffers containing other excipients or auxiliaries as are known in the art of pharmaceutical formulation, Additionally, suspensions of the active compounds may be prepared in a lipophilic vehicle, Suitable lipophilic vehicles include fatty oils such as sesame oil, synthetic fatty acid esters such as ethyl oleate and triglycerides, or materials such as liposomes.

Aqueous injection suspensions may contain substances that increase the viscosity of the suspension, such as sodium carboxymethyl cellulose, sorbitol, or dextran, Formulations for injection may be presented in unit dosage form, e.g., in ampoules or in multi-dose -95 -containers, Alternatively, the active ingredient may be in powder form for constitution with a suitable vehicle, e.g., sterile, pyrogen-free water, before use.

In addition to the formulations described supra, the compounds of the invention may also be formulated as a depot preparation. Such long acting formulations may be administered by implantation (for example, subcutaneously or intramuscularly) or by intramuscular or subcutaneous injection.

The compounds of the invention may be formulated for this route of administration with suitable polymeric or hydrophobic materials (for instance, in an emulsion with a pharmacologically acceptable oil), with ion exchange resins, or as a sparingly soluble to derivative such as, without limitation, a sparingly soluble salt, For administration by inhalation, the compounds of the invention can be delivered in the form of an aerosol spray using a pressurized pack or a nebulizer and a suitable propellant, e.g., without limitation, dichlorodifluoromethane, trichlorofluoromethane, dichlorotetrafluoroethane or carbon dioxide. In the case of a pressurized aerosol, the dosage IS unit maybe controlled by providing a valve to deliver a metered amount, Capsules and cartridges of; for example, gelatin for use in an inhaler or insufflator may be formulated containing a powder mix of the compound and a suitable powder base such as lactose or starch, The compounds of the invention may have favourable pharmacokinetic and pharmacodynamic properties providing systemic availability from oral administration and ingestion. Therefore after ingestion by the animal to be protected, parasiticidally effective concentrations of a compound of the invention in the bloodstream may protect the treated animal from blood-sucking pests such as fleas, ticks and lice. Therefore of note is a composition for protecting an animal from an invertebrate parasite pest in a form for oral administration (i.e. comprising, in addition to a parasiticidally effective amount of a compound of the invention, one or more carriers selected from binders and fillers suitable for oral administration and feed concentrate carriers).

For oral administration in the form of solutions (the most readily available form for absorption), emulsions, suspensions, pastes, gels, capsules, tablets, boluses, powders, granules, rumen-retention and feed/water/lick blocks, the compounds of the invention can be formulated with binders/fillers known in the art to be suitable for oral administration compositions, such as sugars and sugar derivatives (e.g., lactose, sucrose, mannitol, sorbitol), starch (e.g., maize starch, wheat starch, rice starch, potato starch), cellulose and derivatives (e.g., methylcellulose, carboxymethylcellulose, ethylhydroxycellulose), protein derivatives -96 - (e.g., zein, gelatin), and synthetic polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone). if desired, lubricants (e.g., magnesium stearate), disintegrating agents (e.g., cross-linked polyvinylpyrrolidinone, agar, alginic acid) and dyes or pigments can be added. Pastes and gels often also contain adhesives (e.g., acacia, alginic acid, bentonite, cellulose, xanthan gum, colloidal magnesium aluminum silicate) to aid in keeping the composition in contact with the oral cavity and not being easily ejected.

In one embodiment a composition of the present invention is formulated into a chewable and/or edible product (e.g., a chewable treat or edible tablet). Such a product would ideally have a taste, texture and/or aroma favored by the animal to be protected so as to to facilitate oral administration of the compounds of the invention.

If the parasiticidal compositions are in the form of feed concentrates, the carrier is typically selected from high-performance feed, feed cereals or protein concentrates.

Such feed concentrate-containing compositions can, in addition to the parasiticidal active ingredients, comprise additives promoting animal health or growth, improving quality IS of meat from animals for slaughter or otherwise useful to animal husbandry.

These additives can include, for example, vitamins, antibiotics, chemotherapeutics, bacteriostats, fungi stats, cocci di ostats and hormones.

The compound of the invention may also be fonnulated in rectal compositions such as suppositories or retention enemas, using, e.g., conventional suppository bases such as cocoa butter or other glycerides.

The fonnulations for the method of this invention may include an antioxidant, such asBHT (butylated hydroxytoluene). The antioxidant is generally present in amounts of at 0.1-percent (wt/vol). Some of the formulations require a solubilizer, such as oleic acid, to dissolve the active agent, particularly if spinosad is included, Common spreading agents used in these pour-on foniiulations include isopropyl myristate, isopropyl palmitate, caprylic/capric acid esters of saturated C12-C18 fatty alcohols, oleic acid, oleyl ester, ethyl oleate, triglycei'ides, silicone oils and dipropylene glycol methyl ether, The pour-on formulations for the method of this invention are prepared according to known techniques.

Where the pour-on is a solution, the parasiticide/insecticide is mixed with the carrier or vehicle, using heat and stirring if required, Auxiliary or additional ingredients can be added to the mixture of active agent and carrier, or they can be mixed with the active agent prior to the addition of the carrier, Pour-on formulations in the form of emulsions or suspensions are similarly prepared using known techniques.

-97 -Other delivery systems for relatively hydrophobic pharmaceutical compounds may be employed. Liposomes and emulsions are well-known examples of delivery vehicles or carriers for hydrophobic drugs. In addition, organic solvents such as dimethylsulfoxide may be used, if needed.

The rate of application required for effective parasitic invertebrate pest control (e.g. "pesticidally effective amount") will depend on such factors as the species of parasitic invertebrate pest to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like, One skilled in the art can easily determine the pesticidally effective amount to necessary for the desired level of parasitic invertebrate pest control.

In general for veterinary use, the compounds of the invention are administered in a pesticidally effective amount to an animal, particularly a homeothermic animal, to be protected from parasitic invertebrate pests.

A pesticidally effective amount is the amount of active ingredient needed to achieve IS an observable effect diminishing the occurrence or activity of the target parasitic invertebrate pest. One skilled in the art will appreciate that the pesticidally effective dose can vary for the various compounds and compositions useful for the method of the present invention, the desired pesticidal effect and duration, the target parasitic invertebrate pest species, the animal to be protected, the mode of application and the like, and the amount needed to achieve a particular result can be determined through simple experimentation, For oral or parenteral administration to animals, a dose of the compositions of the present invention administered at suitable intervals typically ranges from about 0,0] mg/kg to abouti 00 mg/kg, and preferably from about 0.01 mg/kg to about 30 mg/kg of animal body weight.

Suitable intervals for the administration of the compositions of the present invention to animals range from about daily to about yearly. Of note are administration intervals ranging from about weekly to about once every 6 months. Of particular note are monthly adminstration intervals (i,e, administering the compounds to the animal once every month), The present invention also provides a method for controlling pests (such as mosquitoes and other disease vectors; see also http://www.who,int/malaria/vectorcontrol/irs/en/), In one embodiment, the method for controlling pests comprises applying the compositions of the invention to the target pests, to their locus or to a surface or substrate by brushing, rolling, spraying, spreading or dipping, By way of example, an IRS (indoor residual spraying) -98 -application of a surface such as a wall, ceiling or floor surface is contemplated by the method of the invention, in another embodiment, it is contemplated to apply such compositions to a substrate such as non-woven or a fabric material in the form of(or which can be used in the manufacture of) netting, clothing, bedding, curtains and tents.

In one embodiment, the method for controlling such pests comprises applying a pesticidally effective amount of the compositions of the invention to the target pests, to their locus, or to a surface or substrate so as to provide effective residual pesticidal activity on the surface or substrate, Such application may be made by bmshing, rolling, spraying, spreading or to dipping the pesticidal composition of the invention. By way of example, an IRS application of a surface such as a wall, ceiling or floor surface is contemplated by the method of the invention so as to provide effective residual pesticidal activity on the surface. In another embodiment, it is contemplated to apply such compositions for residual control of pests on a substrate such as a fabric material in the form of (or which can be used in the manufacture IS of) netting, clothing, bedding, curtains and tents.

Substrates including non-woven, fabrics or netting to be treated may be made of natural fibres such as cotton, raffia, jute, flax, sisal, hessian, or wool, or synthetic fibres such as polyamide, polyester, polypropylene, polyacrvlonitrile or the like. The polyesters are particularly suitable, The methods of textile treatment are know, e.g. from Handbuch Textilveredlung: Band 1: AusrUstung, Band 2: Farbgebung, Band 3: Beschichtung, Band 4: Umwelttechnik; Verlag: Deutscher Fachverlag; Auflage: 15., uberarbeitete Ausgabe (17.

April 2006); ISBN-b: 3866410123; ISBN-13: 978-3866410121, see especially Band 1: Ausrustung pages 27-198, more preferably on page 118; or W02008151984 or W02003034823 or U5563 1072 or W0200564072 or W020061 28870 or EPI 724392 or W02005064072 or W02005 113886 or W02007090739.

The term "plant" as used herein includes seedlings, bushes and trees.

The term "crops" or "plant" is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.

-99 -Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins, from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as 6-endotoxins, e.g. Crv]Ab, Cry] Ac, CryiF, Cry]Fa2, Cry2Ab, Crv3A, Cry3Bbl orCry9C, or vegetative insecticidal proteins (Vip), e.g. Vipi, Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp., or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins; agglutinins; proteinase inhibitors, such as trvpsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroidoxidase, ecdysteroid-I.JDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors, H1.VIG-COA-reductase, ion channel blockers, such as blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.

In the context of the present invention there are to be understood by 5-endotoxins, for example CriAb, CriAc, CryiF, CrvlFa2, Cry2Ab, Cry3A, Cry3BbI or Crv9C, or vegetative insecticidal proteins (Yip), for example Vipl, Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by anew combination of different domains of those proteins (see, for example, WO 02/15701). Truncated toxins, for example a truncated CrylAb, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3AOS5, a cathepsin-G-recognition sequence is inserted into a Cry3A toxin (see WO 03/018810).

Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278, WO 95/3 4656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.

-100-The processes for the preparation of such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. Cryl-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0 367 474, EP-A-O 401 979 and WO 90/1365 1.

The toxin contained in the trarisgenic plants imparts to the plants tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera), to Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available.

Examples of such plants are: YieldGard® (maize variety that expresses a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb 1 toxin); YieldGard Plus® (maize variety that expresses a CrylAb and a Cry3BbI toxin); Starlink® (maize variety that IS expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cryl Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylAc toxin); Boilgard I® (cotton variety that expresses a Crv Ac toxin); Bollgard LI® (cotton variety that expresses a CrylAc and a Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and a CrylAb toxin); NewLeaf® (potato variety that expresses a Cry3A toxin); NatureGard ®, Agrisure® GT Advantage (GA2 glyphosate-tolerant trait), Agrisure® CB Advantage (Btl I corn borer (CB) trait) and Protecta®, Further examples of such transgenic crops are: I. Btl I Maize from Syngenta Seeds SAS, Chemin de IHobit 27, F-3 1 790 St. Sauveur, France, registration number C/FRI9o/05/1O, Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinict nub//al/s and Sesarnia nonagrioldes) by transgenic expression of a truncated CrylAb toxin. Btl 1 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

2. Bt176 Maize from Syngenta Seeds SAS. Chemin de l'Hobit 27, F-3 1 790 St. Sauveur, France, registration number C/FR196/O5/iO, Genetically modified Zea mays which has been -101-rendered resistant to attack by the European corn borer (Os/i/n/a nub//al/s and Sesamia nonagnoedes) by transgenic expression of a Cry lAb toxin, Bt176 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

3. M1R604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-3 1 790 St. Sauveur, France, registration number C/FR196/05/10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Crv3AOSS modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/0188th, I0 4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-I 150 Bmssels, Belgium, registration number C1DE/02/9. MON 863 expresses a Crv3Bbt toxin and has resistance to certain Coleoptera insects.

iS 5. IPC 531 Cotton from Monsanto Europe SA. 270-272 Avenue de Tervuren, B-I 150 Bmssels, Belgium, registration number C/ES/96/02.

6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-I 160 Brussels, Belgium, registration number C/NL/00/10. Genetically modified maize for the expression of the protein Cry tF for achieving resistance to certain Lepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium.

7. NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-llSO Brussels, Belgium, registration number C/GB/02/M3/03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 >< MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacter/urn spp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a Cryl Ab toxin obtained from Rae/Ibis thuringiensis suhsp.

kurstak/ which brings about tolerance to certain Lepidoptera, include the European corn borer, The activity of the compositions according to the invention can be broadened considerably, and adapted to prevailing circumstances, by adding other insecticidally, acaricidally and/or fungicidally active ingredients. The mixtures of the compounds of formula I with other -102-insecticidally, acaricidally and/or fungicidally active ingredients may also have further surprising advantages which can also be described, in a wider sense, as synergistic activity.

For example, better tolerance by plants, reduced phytotoxicity, insects can be controlled in their different development stages or better behaviour during their production, for example during grinding or mixing, during their storage or during their use.

Suitable additions to active ingredients here are, for example, representatives of the following classes of active ingredients: organophosphorus compounds, nitrophenol deri-vatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, ureas, pyrrole derivatives, carbamates, pyrethroi ds, chlorinated hydrocarbons, acylureas, pyridyl-to methyleneamino derivatives, macrolides, neonicotinoids and Bacillus thuringiensi s preparations.

The following mixtures of the compounds of formula 1 with active ingredients are preferred (the abbreviation "TX" means "one compound selected from the group consisting of one IS specific compound listed in Table (compounds IL to 1.75) or one specific compound listed in Table A (compounds 1 to 7) of the present invention"): an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX, an acaricide selected from the group of substances consisting of 1,1 -bis(4-chlorophenyl)-2-ethoxyethanol (IIJPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (IUPAC/Chemical Abstracts name) (1059) + TX, 2-fluoro-7\T-methyl-7\T-1-naphthylacetamide (HJPAC name) (1295) -TX, 4-chlorophenyl phenyl sulfone (HJPAC name) (981) + TX, abamectin (1) + TX, acequinocyl (3) + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha-cypermethrin (202) + TX, amidithion (870) + TX, amidoflumet [CCN] + TX, amidothioate (872) + TX, amiton (875) + TX, amiton hydrogen oxalate (875) + TX, amitraz (24) + TX, aramite (881) + TX, arsenous oxide (882) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azobenzene (TUPAC name) (888) + TX, azocyclotin (46) + TX, azothoate (889) + TX, benomyl (62) + TX, benoxafos (alternative name) [CCN] + TX, benzoximate (71) + TX, benzyl benzoate (IIJPAC name) [CCN] + TX, bifenazate (74) + TX, bifenthrin (76) + TX, binapacryl (907) + TX, brofenvalerate (alternative name) + TX, bromocyclen (918) + TX, bromophos (920) + TX, bromophos-ethyl (921) + TX, bromopropylate 94) + TX, -103 -buprofezin (99) + TX, butocarboxim (103) + TX, butoxycarbaxim (104) + TX, butylpyridaben (alternative name) + TX, calcium polysulfide (IIJPAC name) (iii) + TX, camphechlor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbophenothion (947) + TX, CGA 50'439 (development code) (125) + TX, chinomethionat (126) + TX, chlorbenside (959) + TX, chiordimeform (964) + TX, chiordimeform hydrochloride (964) + TX, chlorfenapyr (130) + TX, chlorfenethol (968) + TX, chlorfenson (970) + TX, chlorfensulphide (971) + TX, chlorfenvinphos (131) + TX, chlorobenzilate (975) + TX, chloromebuform (977) + TX, chloromethiuron (978) + TX, chloropropylate (983) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, to chlorthiophos (994) + TX, cinerin 1(696) + TX, cinerin 11(696) + TX, cinerins (696) + TX, clofentezine (158) + TX, closantel (alternative name) [CCNI + TX, coumaphos (174) + TX, crotamiton (alternative name) [CCN] + TX, crotoxyphos (1010) + TX, cufraneb (1013) + TX, cyanthoate (1020) + TX, cyflumetofen (CAS Reg, No.: 400882-07- 7) + TX, cyhalothrin (196) + TX, cyhexatin (199) + TX, cypermethrin (201) + TX, is DCPM 0032) + TX, DDT (2l9)+ TX, demephion (1037) + TX, dernephion-O (1037)+ TX, demephion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-O (1038) + TX, demeton-O-methyl (224)+ TX, demeton-S (1038)+ TX, demeton-S-methyl (224) + TX, derneton-S-methylsulphon (1039) + TX, diafenthiuron (226) + TX, dialifos (1042) + TX, diazinon (227) + TX, dichlofluanid (230) + TX, dichlorvos (236) + TX, dicliphos (alternative name) + TX, dicofol (242) + TX, dicrotophos (243) + TX, dienochlor (1071) + TX, dimefox (1081) + TX, dimethoate (262) + TX, dinactin (alternative name) (653) + TX, dinex (1089) + TX, dinex-diclexine (1089) + TX, dinobuton (269) + TX, dinocap (270) + TX, dinocap-4 [CCN] + TX, dinocap-6 [CCN] + TX, dinocton (1090) + TX, dinopenton (1092) + TX, dinosulfon (1097) + TX, dinoterbon (1098) + TX, dioxathion (1102) + TX, diphenyl sulfone (ILTPAC name) (1103) + TX, disulfiram (alternative name) [CCN] + TX, disulfoton (278) + TX, DNOC (282) + TX, dofenapyn (1113) + TX, doramectin (alternative name) [CCN] + TX, endosulfan (294)+ TX, endothion (1121)+ TX, EPN (297)+ TX, eprinomectin (alternative name) [CCNI + TX, ethion (309) + TX, ethoate-methyl (1134) + TX, etoxazole (320) + TX, etrimfos (1142) + TX, fenazaflor (1147) + TX, fenazaquin (328) + TX, fenbutatin oxide (330) + TX, fenothiocarb (337) + TX, fenpropathrin (342) + TX, fenpyrad (alternative narne)+ TX, fenpyroximate (345)+ TX, fenson (l157)+ TX, fentrifanil (1161) + TX, fenvalerate (349) + TX, fipronil (354) + TX, fluacrypyrim (360) + TX, fluazuron (1166) + TX, flubenzimine (1167) + TX, flucycloxuron (366) + TX, -104-flucythrinate (367) + TX, fluenetil (1169) + TX, flufenoxuron (370) + TX, flumethrin (372) + TX, fluorbenside (1174) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, fonrietanate (405) + TX, fonnetanate hydrochloride (405) + TX, formothion (1192) + TX, formparanate (1193) + TX, gamma-HCH (430) + TX, glyodin (1205) + TX, halfenprox (424) + TX, heptenophos (432) + TX, hexadecyl cyclopropanecarboxylate (IUPAC/Chemical Abstracts name) (1216) + TX, hexythiazox (441) + TX, iodomethane (IUPAC name) (542) + TX, isocarbophos (alternative name) (473) + TX, isopropyl O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin 1(696) + TX, jasmolin 11(696) to + TX, jodf'enphos (1248)+ TX, lindane(430)+ TX, lufenuron (490)+ TX, malathion (492) + TX, malonoben (1254) + TX, mecarbam (502) + TX, mephosfolan (1261) + TX, mesulfen (alternative name) [CCN] + TX, methacrifos (1266) + TX, methamidophos (527) + TX, methidathion (529) + TX, methiocarb (530) + TX, methomyl (531) + TX, methyl bromide (537) + TX, metolcarb (550) + TX, mevinphos (556) + TX, mexacarbate is (1290) + TX, milbemectin (557) + TX, niilbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, monocrotophos (561) + TX, morphothion (1300) + TX, moxidectin (alternative name) CCNj + TX, naled (567) + TX, NC-184 (compound code) + TX, NC-S 12 (compound code) + TX, nifluridide (1309)+ TX, nikkomycins (alternative name) [CCNI + TX, nitrilacarb (1313) + TX, nitrilacarb 1:1 zinc chloride complex (1313) + TX, NNT-0101 (compound code) + TX, NNT-0250 (compound code) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxydeprofos (1324) + TX, oxydisulfoton ( 325) + TX, pp'-DDT (219) + TX, parathion (615) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, phenlcapton (1330) + TX, phenthoate (631)+ TX, phorate(636)+ TX, phosalone (637)+ TX, phosfolan (1338) + TX, phosmet (638) + TX, phosphamidon (639) + TX, phoxim (642) + TX, pirimiphos-methyl (652) + TX, polychloroterpenes (traditional name) (1347) + TX, polynactins (alternative name) (653) + TX, proclonol (1350) + TX, profenofos (662) + TX, promacyl (1354) + TX, propargite (671) + TX, propetamphos (673) + TX, propoxur (678) + TX, prothidathion (1360) + TX, prothoate (1362) + TX, pyrethrin 1(696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridaphenthion (701) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, quinalphos (711) + TX, quintiofos (1381)+ TX, R-1492 (development code) (1382) + TX, RA-17 (development code) (1383) + TX, rotenone (722) + TX, schradan (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, -105 -sophamide (1402) + TX, spirodiclofen (738) + TX, spiromesifen (739) + TX, SSI-121 (development code) (1404) + TX, sulfiram (alternative name) [CCN] + TX, suifluramid (750) + TX, sulfotep (753) + TX, sulphur(754)+ TX, SZI-121 (development code) (757) + TX, tau-fluvalinate (398) + TX, tebufenpyrad (763) + TX, TEPP (1417) + TX, terbam (alternative name) + TX, tetrachlorvinphos (777) + TX, tetradifon (786) + TX, tetranactin (alternative name) (653) + TX, tetrasul (1425) + TX, thiafenox (alternative name) + TX, thiocarboxime (1431) + TX, thiofanox (800) + TX, thiometon (801) + TX, thioquinox (1436) + TX, thuringiensin (alternative name) [CCN] + TX, triamiphos (1441) + TX, triarathene (1443) + TX, triazophos (820) + TX, triazuron (alternative name) + to TX, trichlorfon (824) + TX, trifenofos (1455) + TX, trinactin (alternative name) (653) + TX, vamidothion (847) + TX, vaniliprole [CCN] and YI-5302 (compound code) + TX, an algicide selected from the group of substances consisting of bethoxazin [CCN] + TX, copper dioctanoate (IUPAC name) (170) + TX, copper sulfate (172) + TX, cybutryne [CCN] + TX, dichlone (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, IS fentin (347) + TX, hydrated lime [CCNI + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamid (1379) + TX, simazine (730) + TX, triphenyltin acetate (IIJPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, an anthelmintic selected from the group of substances consisting of abamectin () + TX, crufomate (1011) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCNI + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCNJ + TX, selamectin (alternative name) [CCNI + TX, spinosad (737) and thiophanate (1435) + TX, an avicide selected from the group of substances consisting of chloralose (127) + TX, endrin (1122) + TX, fenthion (346) + TX, pyridin-4-amine (ITJPAC name) (23) and strychnine (745) + TX, a bactericide selected from the group of substances consisting of 1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCNJ + TX, dichlorophen (232) + TX, dipyrithione (1105) + TX, dodicin (1112) + TX, fenaminosulf(l 144) + TX, formaldehyde (404) + TX, hydrargaphen (alternative name) [CCNI + TX, kasugamycin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX, nickel bis(dimethyldithiocarbamate (IUPAC name) (1308) + TX, nitrapyrin (580) -106- + TX, octhilinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, tecloflalam (766) + TX, and thiomersal (alternative name) [CCN] + TX, a biological agent selected from the group of substances consisting of Adoxophycs orana GY (alternative name) (12) + TX, Agrobacier/um radiobacler (alternative name) (13) + TX, Amblyseius spp. (alternative name) (19) + TX, Anagraphafàicifèra NPV (alternative name) (28) + TX, Anagrus afomus (alternative name) (29) + TX, Aphelinus abdominal/s (alternative name) (33) + TX, Aphidius colemani (alternative name) (34) + TX, to Aphidoletes aphidimyza (alternative name) (35) + TX, A ulographa californica N PV (alternative name) (38) + TX, Bacillus jirmus (alternative name) (48) + TX, Bacillus sphaericus Neide (scientific name) 49) + TX, Bacillus thuringiensis Berliner (scientific name) (51) + TX, Bacillus thuringiensis subsp. aizawai (scientific name) (51) + TX, Bacillus thuring/ensis subsp. israeiens/s (scientific name) (Si) + TX, Bacillus Ihur/ug/ensis IS subsp. japonencis (scientific name) (51) + TX, Bacillus thuringiensis subsp. kurstaki (scientific name) (51) + TX, Bacillus thuringiensis subsp. tenebrionis (scientific name) (51) + TX, Beauveria hassiana (alternative name) (53) + TX, Beauveria hrongniartii (alternative name) (54) + TX, Chrysoperla carizea (alternative name) (151) + TX, Czyptoiaemus montrouzieri (alternative name) (178) + TX, C)diapomonella GV (alternative name) (191) + TX, Dacnusa sib/rica (alternative name) (212) + TX, Diglyphus isaea (alternative name) (254) + TX, Encarsiaformosa (scientific name) (293) + TX, Erelmocerits' eremicus (alternative name) (300) + TX, Helicoverpa zea NPV (alternative name) (43 1) + TX, Heterorhabditis bacteriophora and H. megidis (alternative name) (433) + TX, H4npodamia convergens (alternative name) (442) + TX, Leptornasux daclylopii (alternative name) (488) + TX, iVacrolophus caliginosus (alternative name) (491) + TX, )tfameswa hrassicae NPV (alternative name) (494) + TX, Afetaphycus helvolus (alternative name) (522) + TX, A'Ietarhizium an/sopliae var, acridum (scientific name) (523) + TX, Ivietarhizium anisopliae var, anisopliae (scientific name) (523) + TX, Neodirion sertitèr NPV and N lecontei NPV (alternative name) (575) + TX, Onus spp.

(alternative name) (596) + TX, Paec/loniycesfiimosoroseus (alternative name) (613) + TX, Phytose/uiuspersimiiis (alternative name) (644) + TX, Spodoplera exigua multicapsid nuclear polyhedrosis vims (scientific name) (74) + TX, Steinernema hihionis (alternative name) (742) + TX, Steinernema catpocapsae (alternative name) (742) + TX, Steinernema fell/ac (alternative name) (742) + TX, Sleinernema glaseni (alternative name) (742) + TX, -107-Steinernerna nobrat'e (alternative name) (742) + TX, Sleinernerna riobravis (alternative name) (742) + TX, Steinernema scapleresce (alternative name) (742) + TX, Si elnernerna spp. (alternative name) (742) + TX, Trichogramma spp. (alternative name) (826) + TX, iyphiodroinus occidenialis (alternative name) (844) and Verticilliurn iecanii (alternative name) (848) + TX, a soil sterilant selected from the group of substances consisting of iodomethane (IUPAC name) (542) and methyl bromide (537) + TX, a chemosterilant selected from the group of substances consisting of apholate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, to diflubenzuron (250) + TX, dimatif(alternative name) [CCNJ + TX, hemel [CCN] + TX, hempa [CCX] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl apholate [CCN] + TX, morzid [CCX] + TX, penfluron (alternative name) [CCN] + TX, tepa [CCN] + TX, thiohempa (alternative name) [CCN] + TX, thiotepa (alternative name) [CCN] + TX, tretamine (alternative name) [CCNJ and uredepa (alternative name) [CCNJ + IS TX, an insect pheromone selected from the group of substances consisting of (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-l-ol (IUPAC name) (222) + TX, (ic)-tridec-4-en-]-yl acetate (IUPAC name) (829) + TX, (F)-6-methylhept-2-en-4-ol (IUPAC name) (54]) + TX, (F, Z)-tetradeca-4, 1 0-dien-1-yl acetate (IUPAC name) (779) + TX, (Z)-dodec-7-en-1-yl acetate (IUPAC name) (285) + TX, (Z)-hexadec-I 1-enal (IUPAC name) (436) + TX, (Z)-hexadec-] ]-en-]-yl acetate (IIJPAC name) (437)+ TX, (Z)-hexadec-]3-en-l l-yn-l-yl acetate (IUPAC name) (438)+ TX, (Z)-icos-]3-en-l0-one (IUPAC name) (448)+ TX, (Z)-tetradec-7-en-1-al (IIJPAC name) (782) + TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783) + TX, (Z)-tetradec-9-en-L-yl acetate (LUPAC name) (784) + TX, (7E,9Z)-dodeca- 7,9-dien-1-yl acetate (RJPAC name) (283)+ TX, (9Z,]]F)-tetradeca-9,1]-dien-]-yI acetate (ILTPAC name) (780) + TX, (9Z, 12E)-tetradeca-9,12-dien-]-yl acetate (IUPAC name) (78) + TX, 14-methyloctadec-1-ene (IUPAC name) (545) + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one (IUPAC name) (544) + TX, alpha-multistriatin (alternative name) [CCN] + TX, brevicomin (alternative name) [CCNI + TX, codlelure (alternative name) [CCN] + TX, codlemone (alternative name) (t67) + TX, cuelure (alternative name) (179) + TX, disparlure (277) + TX, dodec-8-en-1-yl acetate (IUPAC name) (286) + TX, dodec- 9-en-]-yl acetate (IUPAC name) (287)+ TX, dodeca-8 + TX, l0-dien-l-yl acetate (IUPAC name) (284) + TX, dominicalure (alternative name) [CCN] + TX, ethyl 4-methyloctanoate (JUPAC name) (317) + TX, eugenol (alternative name) [CCN] + TX, frontalin (alternative -108-name) [CCNJ + TX, gossyplure (alternative name) (420) + TX, grandlure (421) + TX, grandlure I (alternative name) (421) + TX, grandlure 11 (alternative name) (421) + TX, grandlure Ill (alternative name) (421) + TX, grandlure IV (alternative name) (421) + TX, hexalure [CCN] + TX, ipsdienol (alternative name) [CCN] + TX, ipsenol (alternative name) [CCN] + TX, japonilure (alternative name) (481) + TX, lineatin (alternative name) [CCN] + TX, litlure (alternative name) [CCN] + TX, looplure (alternative name) [CCN] + TX, medlure [CCNI + TX, megatomoic acid (alternative name) [CCN] + TX, methyl eugenol (alternative name) (540) + TX, muscalure (563) + TX, octadeca-2,13-dien-i-yl acetate (IUPAC name) (588) + TX, octadeca-3,13-dien-1-yl acetate (IUPAC name) (589) + to TX, orfralure (alternative name) [CCN] + TX, oryctalure (alternative name) (317) + TX, ostramone (alternative name) [CCN] + TX, siglure [CCN] + TX, sordidin (alternative name) (736) + TX, sulcatol (alternative name) [CCN] + TX, tetradec-1 1-en-i-yl acetate (IUPAC name) (785) + TX, trimedlure (839) + TX, trimedlure A (alternative name) (839) + TX, trimedlure B1 (alternative name) (839) + TX, trimedlure B2 (alternative name) (839) is + TX, trimedlure C (alternative name) (839) and trunc-call (alternative name) [CCN] + TX, an insect repellent selected from the group of substances consisting of 2-(octylthio)ethanol (IUPAC name) (591) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936)+ TX, dibutyl adipate(IUPAC name) (1046) + TX, dibutyl phthalate (1047)+ TX, dibutyl succinate (IUPAC name) (1048) + TX, diethyltoluamide [CCNI -TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1137) + TX, hexamide [CCN + TX, methoquin-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] and picaridin [CCNJ + TX, an insecticide selected from the group of substances consisting of 1-dichloro-1-nitroethane (IUPAC/Chemical Abstracts name) (1058) + TX, , I -dichloro-2,2-bis(4-ethylphenyl)ethane (I[JPAC name) (1056), + TX, ,2-dichloropropane (ITJPAC/Chemical Abstracts name) (1062) + TX, I,2-dichloropropane with I,3-dichloropropene (IIJPAC name) (1063) + TX, 1-bromo-2-chloroethane (IUPAC/Chemical Abstracts name) (916) + TX, 2,2,2-trichloro-1- (3,4-dichlorophenyl)ethyl acetate (LUPAC name) (1451) + TX, 2,2-dichlorovinyl 2- ethylsulphinylethyl methyl phosphate (IIJPAC name) (1066) + TX, 2-O,3-dithiolan-2- yl)phenyl dimethylcarbamate (IUPAC/ Chemical Abstracts name) (1109) + TX, 2-(2- butoxyethoxy)ethyl thiocyanate (IUPAC/Chemical Abstracts name) (935) + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate (IUPAC/ Chemical Abstracts name) (1084) + TX, 2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name) (986) + TX, 2-chlorovinyl diethyl phosphate (IUPAC name) (984) + TX, 2-imidazolidone (TUPAC name) (1225) + -109- TX, 2-isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate (IUPAC name) (1284) + TX, 2-thiocyanatoethyl laurate(IUPAC name) (433)+ TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917) + TX, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name) (1283) + TX, 4- methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate (TUPAC name) (1285) + TX, 5,5-dimethyl-3 -oxocyclohex-1 -enyl dimethylcarbamate (IUPAC name) (1085) + TX, abamectin (1) + TX, acephate (2) + TX, acetamiprid (4) + TX, acethion (alternative name) [CCN] + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, acrylonitrile (IUPAC name) (861) + TX, alanycarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863)+ TX, aldrin (864) + to TX, allethrin (17) + TX, allosamidin (alternative name) [CCNJ + TX, allyxycarb (866) + TX, alpha-cypermethrin (202) + TX, alpha-ecdysone (alternative name) [CCN] + TX, aluminium phosphide (640) + TX, amidithion (870) + TX, amidothioate (872) + TX, aminocarb (873) + TX, amiton (875) + TX, amiton hydrogen oxalate (875) + TX, amitraz (24) + TX, anabasine (877) + TX, athidathion (883) + TX, AVI 382 (compound code) + is TX, AZ 60541 (compound code) + TX, azadirachtin (alternative name) (4]) + TX, azamethiphos (42) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azothoate (889) + TX, Bacillus tintringiensis delta endotoxins (alternative name) (52) + TX, barium hexafluorosilicate (alternative name) [CCNI + TX, barium polysulfide (IUPAC/Chemical Abstracts name) (892) + TX, barthrin [CCNI + TX, Bayer 22/190 (development code) (893) + TX, Bayer 22408 (development code) (894) + TX, bendiocarb (58) + TX, benfuracarb (60) + TX, bensultap (66) + TX, beta-cyfluthrin (194) + TX, beta-cypermethrin (203) + TX, bif'enthrin (76) + TX, bioallethrin (78) + TX, bioallethrin S-cyclopentenyl isomer (alternative name) (79) + TX, bioethanomethrin [CCN] + TX, biopermethrin (908) + TX, bioresmethrin (80) + TX, bis(2-chloroethyl) ether (IUPAC name) (909) + TX, bistrifluron (83) + TX, borax (86) + TX, brofenvalerate (alternative name) + TX, bromfenvinfos (9]4) + TX, bromocyclen (9]8) + TX, bromo-DDT (alternative name) [CCNJ + TX, bromophos (920) + TX, bromophos-ethyl (921) + TX, bufencarb (924) + TX, buprofezin (99) + TX, butacarb (926) + TX, butathiofos (927) + TX, butocarboxim (103) + TX, butonate (932) + TX, butoxycarboxim (104) + TX, butylpyridaben (alternative name) + TX, cadusafos (109) + TX, calcium arsenate [CCNJ + TX, calcium cyanide (444) + TX, calcium polysulfide (IUPAC name) (ill) + TX, camphechlor (941) + TX, carbanolate (943) + TX, carbaryl (]]5) + TX, carbofuran (] ] 8) + TX, carbon disulfide (IUPAC/Chemical Abstracts name) (945) + TX, carbon tetrachloride (IUPAC name) (946) + TX, carbophenothion 947) + TX, carbosulfan (119) + TX, cartap (123) + TX, cartap hydrochloride (123) + TX, cevadine (alternative name) (725) + TX, chlorbicyclen (960) + TX, chlordane (128) + TX, chlordecone (963) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorethoxyfos (129) + TX, chlorfenapyr (130) + TX, chlorfenvinphos (131) + TX, chlorfluazuron (132) + TX, chiormephos (136) + TX, chloroform [CCN] + TX, chloropicrin (141) + TX, chiorphoxim (989) + TX, chlorprazophos (990) + TX, chlorpyrifos (145) + TX, chiorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX, chromafenozide (150) + TX, cinerin 1(696) + TX, cinerin 11(696) + TX, cinerins (696) + TX, cis-resmethrin (alternative name) + TX, cismethrin (80) + TX, clocythrin (alternative name) + TX, to cloethocarb (999) + TX, closantel (alternative name) [CCN] + TX, clothianidin (165) + TX, copper acetoarsenite [CCN] + TX, copper arsenate [CCNI + TX, copper oleate [CCN] + TX, conmaphos (174) + TX, coumithoate (1006) + TX, crotamiton (alternative name) [CCNJ + TX, crotoxyphos (1010) + TX, crufomate (1011) + TX, cryolite (alternative name) (177) + TX, CS 708 (development code) (1012) + TX, cyanofenphos is (1019) + TX, cyanophos (184) + TX, cyanthoate (1020) + TX, cyclethrin [CCN] + TX, cycloprothrin (188) + TX, cyfluthrin (193) + TX, cyhalothrin (196) + TX, cypermethrin (201) + TX, cyphenothrin (206) + TX, cyromazine (209) + TX, cythioate (alternative name) [CCNI + TX, d-ljmonene (alternative name) [CCN] + TX, d-tetramethrin (alternative name) (788) + TX, DAEP (1031) + TX, dazomet(216) + TX, DDT (219) + TX, decarbofuran (1034) + TX, deltamethrin (223) + TX, demephion (1037) + TX, demephion-O 0037) + TX, demephion-S (1037) + TX, demeton (1038)+ TX, demeton-methyl (224) + TX, demeton-O (1038) + TX, demeton-O-methyl (224) + TX, demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulphon (1039) + TX, diafenthiuron (226) + TX, dialifos (1042) + TX, diamidafos (1044) + TX, diazinon (227) + TX, dicapthon (1050)+ TX, dichlofenthion (1051)+ TX, dichiorvos (236)+ TX, dicliphos (alternative name) + TX, dicresyl (alternative name) [CCNI + TX, dicrotophos (243) + TX, dicyclanil (244) + TX, dieldrin (1070) + TX, diethyl 5-methylpyrazol-3-yl phosphate (IUPAC name) (076) + TX, ditlubenzuron (250) + TX, dilor (alternative name) [CCN] + TX, dimefluthrin [CCN] + TX, dimefox (1081) + TX, dimetan (1085) + TX, dimethoate (262) + TX, dimethrin (1083) + TX, dimethylvinphos (265) + TX, dimetilan (1086) + TX, dinex (1089) + TX, dinex-diclexine (1089) + TX, dinoprop (1093) + TX, dinosam (1094) + TX, dinoseb (1095)+ TX, dinotefuran (271) + TX, diofenolan (1099) + TX, dioxabenzofos (1100) + TX, dioxacarb (1101) + TX, dioxathion (1102) + TX, disulfoton (278) + TX, dithicrofos (1108) + TX, DNOC (282) + TX,

-III -

doramectin (alternative name) [CCN] + TX, DSP (1115) + TX, ecdysterone (alternative name) [CCN] + TX, El 1642 (development code) (1118)+ TX, emamectin (291) + TX, emamectin benzoate (291)+ TX, EMPC (1120) + TX, empenthrin (292)+ TX, endosulfan (294) + TX, endothion (1121) + TX, endrin (1122) + TX, EPBP (1123) + TX, EPN (297) + TX, epofenonae (1124) + TX, eprinomectin (alternative name) [CCN] + TX, esfenvalerate (302) + TX, etaphos (alternative name) [CCN] + TX, ethiofencarb (308) + TX, ethion(309)+ TX, ethiprole (310) + TX, ethoate-methyl (1134)+ TX, ethoprophos (312) + TX, ethyl formate (IUPAC name) [CCN] + TX, ethyl-DDD (alternative name) (1056) + TX, ethylene dibromide (316) + TX, ethylene dichloride to (chemical name) (1136) + TX, ethylene oxide [CCN] + TX, etofenprox (319) + TX, etrimfos (1142) + TX, EXD (1143) + TX, famphur (323) + TX, fenamiphos (326) + TX, fenazaf'lor (1147) + TX, fenchlorphos (1148) + TX, fenethacarb (1149) + TX, fenfluthrin (1150) + TX, fenitrothion (335) + TX, fenobucarb (336) + TX, fenoxacrim (1153) + TX, fenoxycarb (340) + TX, fenpirithrin (1155) + TX, fenpropathrin (342) + TX, fenpyrad IS (alternative name)+ TX, fensulfothion (1158)+ TX, fenthion (346)+ TX, fenthion-ethyl [CCN] + TX, fenvalerate (349) + TX, fipronil (354) + TX, flonicamid (358) + TX, flubendiamide (CAS. Reg, No.: 27245 1-65-7) + TX, flucofuron (1168) + TX, flucycloxuron (366) + TX, flucythrinate (367) + TX, fluenetil (1169) + TX, flufenerim [CCN] + TX, flufenoxuron (370) + TX, flufenprox (1171) + TX, flumethrin (372) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, fonofos (1191) + TX, formetanate (405) + TX, formetanate hydrochloride (405) + TX, forniothion (H 92) + TX, formparanate (1193) + TX, fosmethilan (1194)+ TX, fospirate (L195)+ TX, fosthiazate (408) + TX, fosthietan (1196) + TX, furathiocarb (412) + TX, furethrin (1200) + TX, garnma-cyhalothrin (197) + TX, gamma-HCH (430) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, GY-Si (development code) (423) + TX, halfenprox (424) + TX, halofenozide (425) + TX, HCH (430) + TX, HIEOD (070) + TX, heptachlor (1211) + TX, heptenophos (432) + TX, heterophos [CCN] + TX, hexaflumuron (439) + TX, Hl-IDN (864) + TX, hydramethylnon (443) + TX, hydrogen cyanide (444) + TX, hydroprene (445) + TX, hyquincarb (1223) + TX, imidacloprid (458) + TX, imiprothrin (460) + TX, indoxacarb (465) + TX, iodomethane (TUPAC name) (542)+ TX, IPSP (1229) + TX, isazofos (1231)+ TX, isobenzan (1232)+ TX, isocarbophos (alternative name) (473)+ TX, isodrin (1235)+ TX, isofenphos (1236) + TX, isolane (1237) + TX, isoprocarb (472) + TX, isopropyl O-(methoxy-aminothiophosphoryl)salicylate (IUPAC name) (473) + TX, isoprothiolane (474) + TX, isothioate (1244) + TX, isoxathion (480) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin 1 (696) + TX, jasmolin H (696) + TX, jodfenphos (1248) + TX, juvenile hormone I (alternative name) [CCN] + TX, juvenile hormone II (alternative name) [CCN] + TX, juvenile hormone III (alternative name) [CCN] + TX, kelevan (1249) + TX, kinoprene (484) + TX, lambda-cyhalothrin (198) + TX, lead arsenate [CCN] + TX, lepimectin(CCN)+ TX, leptophos (1250)+ TX, lindme (430) + TX, lirimfos (t251)+ TX, lufenuron (490) + TX, lythidathion (1253) + TX, in-cumenyl methylcarbamate (TUPAC name) (1014) + TX, magnesium phosphide (IUPAC name) (640) + TX, malathion (492) + TX, malonoben (1254) + TX, mazidox (1255) + TX, mecarbam (502) to + TX, mecarphon (1258)+ TX, menazon (1260)+ TX, mephosfolan (1261) + TX, mercurous chloride (513) + TX, mesulfenfos (1263) + TX, metaflumizone (CCN) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, methacrifos (1266) + TX, methamidophos (527) + TX, methanesulphonyl fluoride (IUPAC/Chemical Abstracts name) (1268) + TX, methidathion (529) + TX, IS methiocarb (530) + TX, methocrotophos (1273) + TX, methomyl (531) + TX, methoprene (532) + TX, methoquin-butyl (1276) + TX, methothrin (alternative name) (533) + TX, methoxychlor (534) + TX, methoxyfenozide (535) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, methylchloroform (alternative name) [CCN] + TX, methylene chloride [CCN] + TX, metofluthrin [CCN] + TX, metolcarb (550) + TX, metoxadiazone (1288) + TX, mevinphos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293)+ TX, mirex (1294)+ TX, monocrotophos (561)+ TX, morphothion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naftalofos (alternative name) [CCN] + TX, naled (567) + TX, naphthalene (IIJPAC/Chemical Abstracts name) (1303) + TX, NC-I 70 (development code) (1306) + TX, NC-184 (compound code) + TX, nicotine (578) + TX, nicotine sulfate (578) + TX, nifluridide (1309) + TX, nitenpyram (579) + TX, nithiazine (13 11) + TX, nitrilacarb (13 13) + TX, nitrilacarb 1: 1 zinc chloride complex (1313)+ TX, NNI-0l0l (compound code)+ TX, NNI-0250 (compound code) + TX, nornicotine (traditional name) (1319) + TX, novaluron (585) + TX, noviflumuron (586) + TX, O-5-dichloro-4-iodophenyl 0-ethyl ethylphosphonothioate (IUPAC name) (1057) + TX, 0, 0-diethyl 0-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate (IUPAC name) (1074) + TX, 0,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate (IUPAC name) (1075) + TX, 0,O,O',O'-tetrapropyl dithiopyrophosphate (IUPAC name) (1424) + TX, oleic acid (IUPAC name) (593) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxydemeton-methyl (609) + TX, oxydeprofos (1324) + TX, oxydisulfoton (1325) + TX, pp-DDT (219) + TX, para-dichlorobenzene [CCN] + TX, parathion (615) + TX, parathion-methyl (616)+ TX, penfluron (alternative name) [CCNI + TX, pentachlorophenol (623) + TX, pentachiorophenyl laurate (IIJPAC name) (623) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, PH 60-3 8 (development code) (1328) + TX, phenkapton (1330) + TX, phenothrin (630) + TX, phenthoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phosfolan (1338) + TX, phosmet (638) + TX, phosnichlor (1339) + TX, phosphamidon (639) + TX, phosphine (IUPAC name) (640) + TX, phoxim (642) + TX, phoxim-methyl (1340) + TX, to pirimetaphos (1344) + TX, pirimicarb (65)+ TX, pirimiphos-ethyl (1345) + TX, pirimiphos-methyl (652) + TX, polychlorodicyclopentadiene isomers (ILPAC name) (t346) + TX, polychloroterpenes (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCNJ + TX, prallethrin (655) + TX, precocene I (alternative name) [CCN] + TX, precocene 11 (alternative name) [CCN] + TX, precocene IS Ill (alternative name) [CCN] + TX, primidophos (1349)+ TX, profenofos (662)+ TX, profluthrin [CCN] + TX, promacyl (1354) + TX, promecarb (1355) + TX, propaphos (1356)+ TX, propetamphos(673)+ TX, propoxur(678)+ TX, prothidathion (1360) + TX, prothiofos (686) + TX, prothoate (1362) + TX, prot&enbute [CCN] + TX, pymetrozine (688) + TX, pyraclofos (689) + TX, pyrazophos (693) + TX, pyresmethrin (1367) + TX, pyrethrin 1(696) + TX, pyrethrin H (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridalyl (700) + TX, pyridaphenthion (701) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, pyriproxyfen (708) + TX, quassia (alternative name) [CCN] + TX, quinaiphos (711) + TX, quinaiphos-methyl (1376) + TX, quinothion (1380) + TX, quintiofos (1381) + TX, R-1492 (development code) (1382) + TX, rafoxanide (alternative name) [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 (development code) (1386)+ TX, ryaiña (alternative name) (1387) + TX, ryanodine (traditional name) (1387) + TX, sabadilla (alternative name) (725) + TX, schradan (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCNI + TX, SI-0009 (compound code) + TX, SI- 0205 (compound code) + TX, 51-0404 (compound code) + TX, SI-0405 (compound code) + TX, silafluofen (728) + TX, SN 72129 (development code) (1397) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoride (IUPAC/Chemical Abstracts name) (1399) + TX, sodium hexafluorosilicate (1400) + TX, sodium pentachlorophenoxide (623) + TX, sodium selenate (IUPAC name) (1401) + TX, sodium thiocyanate [CCNJ + TX, sophamide (1402) + TX, spinosad (737) + TX, spiromesifen (739) + TX, spirotetrmat (CCN) + TX, sulcofuron (746) + TX, sulcofuron-sodium (746) + TX, sulfiuramid (750) + TX, sulfotep (753) + TX, sulphuryl fluoride (756) + TX, sulprofos (1408) + TX, tar oils (alternative name) (758) + TX, tau-fluvalinate (398) + TX, tazimcarb (1412) + TX, TDE (1414) + TX, tebufenozide (762) + TX, tebufenpyrad (763) + TX, tebupirimfos (764) + TX, teflubenzuron (768) + TX, tefluthrin (769) + TX, temephos (770) + TX, TEPP (1417) + TX, teraflethrin (1418) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachloroethane [CCN] + TX, tetrachlorvinphos (777) + TX, tetramethrin (787) + TX, theta-cypermethrin (204) + TX, thiacloprid (791) + to TX, thiafenox (alternative name) + TX, thiamethoxam (792) + TX, thicrofos (1428) + TX, thiocarboxime (1431) + TX, thiocyclam (798) + TX, thiocyclam hydrogen oxalate (798) + TX, thiodicarb (799) + TX, thiofanox (800) + TX, thiometon (801) + TX, thionazin (1434) + TX, thiosultap (803) + TX, thiosultap-sodium (803) + TX, thuringiensin (alternative name) [CCN] + TX, tolfenpyrad (809) + TX, tralomethrin (812) is + TX, transfluthrin (813)+ TX, transpermethrin (1440)+ TX, triamiphos(1441)+ TX, triazamate (818) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorfon (824) + TX, thchlormetaphos-3 (alternative name) [CCNj + TX, trichloronat (1452) + TX, trifenofos (1455) + TX, triflumuron (835) + TX, thmethacarb (840) + TX, triprene (1459) + TX, vamidothion (847) + TX, vaniliprole [CCN] + TX, veratridine (alternative name) (725) + TX, veratrine (alternative name) (725) + TX, XMC (853) + TX, xylylcarb (854) + TX, Yl-5302 (compound code) + TX, zeta-cypermethrin (205) + TX, zetamethrin (alternative name) + TX, zinc phosphide (640) + TX, zolaprofos (1469) and ZXI 8901 (development code) (858) + TX, cyantraniliprole [736994-63-19] + TX, chlorantraniliprole [500008-45-7] + TX, cyenopyrafen [560121-52-0] + TX, cyflumetofen [400882-07-71 + TX, pyrifluquinazon [337458-27-2] + TX, spinetoram [187166-40-1 + 187166-15-0] + TX, spirotetramat [2033 13-25-11 + TX, sulfoxaflor [946578-00-3] + TX, flufiproe [704886-18-0] + TX, meperfluthrin [915288-13-0] + TX, tetramethylfluthrin [84937-88-21 + TX, a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (TUPAC name) (913) + TX, bromoacetamide [CCNJ + TX, calcium arsenate [CCN] + TX, cloethocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (IIJPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, trifenmorph (1454) + TX, trimethacarb (840) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (LUPAC name) (347) + TX, pyriprole [394730-71-3] + TX, a nematicide selected from the group of substances consisting ofAKD-3088 (compound code) + TX, 1,2-dibromo-3-chloropropane (IUPAC/Chemical Abstracts name) (1045) + TX, 1,2-dichioropropane (IUPAC/ Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane with 1,3-dichioropropene (IIJPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 3,4-dichiorotetrahydrothiophene 1,1-dioxide (IUPAC/Chemical Abstracts name) (1065) + TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name) (980) + TX, 5-methyl- to 6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPAC name) (1286) + TX, 6-isopentenylaminopurine (alternative name) (210) + TX, abamectin (1) + TX, acetoprole [CCN] + TX, alanycarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, AZ 60541 (compound code) + TX, benclothiaz [CCN] + TX, benomyl (62) + TX, butylpyridaben (alternative name) + TX, cadusafos (109) + TX, carbofuran (118) + TX, IS carbon disulfide (945) + TX, carbosulfan (119)+ TX, chloropicrin (141)+ TX, chiorpyrifos (145) + TX, cloethocarb (999) + TX, cytokinins (alternative name) (210) + TX, dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidafos (1044) + TX, dichlofenthion (1051) + TX, dicliphos (alternative name)+ TX, dimethoate(262)+ TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCNJ + TX, ethoprophos (312) + TX, ethylene dibromide (316)+ TX, fenamiphos (326) + TX, fenpyrad(alternative name)+ TX, fensulfothion (1 158)+ TX, fosthiazate (408) + TX, fosthietan (1196) + TX, furfural (alternative name) [CCN] + TX, GY-81 (development code) (423) + TX, heterophos [CCN] + TX, iodomethane (IUPAC name) (542) + TX, isamidofos (1230) + TX, isazofos (1231) + TX, ivermectin (alternative name) [CCNI + TX, kinetin (alternative name) (210) + TX, mecarphon (1258) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCNI + TX, Mj;rothecium vern1carza composition (alternative name) (565) + TX, NC-184 (compound code) + TX, oxamyl (602) + TX, phorate (636) + TX, phosphamidon (639) + TX, phosphocarb [CCN] + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCNI + TX, spinosad (737) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachlorothiophene (TUPAC/ Chemical Abstracts name) (1422) + TX, thiafenox (alternative name) + TX, thionazin (1434) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, xylenols [CCN] + TX, Y1-5302 (compound code) and zeatin (alternative name) (210) + TX, fluensulfone [318290-98-11 + TX, a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX, a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX, a rodenticide selected from the group of substances consisting of 2-isovalerylindan-1,3-dione to (IUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IIJPAC name) (748) + TX, alpha-chlorohydrin [CCNI + TX, aluminium phosphide (640) + TX, antu (880) + TX, arsenous oxide (882) + TX, barium carbonate (891) + TX, bisthiosemi (912) + TX, brodifacoum (89) + TX, bromadiolone (91) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, IS cholecalciferol (alternative name) (850) + TX, coumachlor (1004) + TX, coumafuryl (1005) + TX, coumatetralyl (175) + TX, crimidine (1009) + TX, difenacoum (246) + TX, difethialone (249) + TX, diphacinone (273) + TX, ergocalciferol (301) + TX, flocoumafen (357)+ TX, fluoroacetamide(379) + TX, flupropadine(1183)+ TX, flupropadine hydrochloride (1183) + TX, gamma-HCH(430) + TX, HCH(430) + TX, hydrogen cyanide (444) + TX, iodomethane (IUPAC name) (542) + TX, lindane (430) + TX, magnesium phosphide (LUPAC name) (640) + TX, methyl bromide (537) + TX, norbormide ( 318) + TX, phosacetim (1336) + TX, phosphine (IUPAC name) (640) + TX, phosphorus [CCN] + TX, pindone (1341) + TX, potassium arsenite [CCN] + TX, pyrinuron (137fl + TX, scilliroside (1390) + TX, sodium arsenite [CCNJ + TX, sodium cyanide (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCX] + TX, warfarin (851) and zinc phosphide (640) + TX, a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934) + TX, 5-( I,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB- 599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex(1393)+ TX, sesasmolin (1394) and sulfoxide (1406) + TX, an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, methiocarb (530) + TX, pyridin-4-amine (TUPAC name) (23) + TX, thiram (804) + TX, trimethacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX, a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX, a wound protectant selected from the group of substances consisting of mercuric oxide (512) to + TX, octhilinone (590) and thiophanate-methyl (802) + TX, and biologically active compounds selected from the group consisting of azaconazole (60207-31-0] + TX, bitertanol [70585-36-3] + TX, bromnconazole [116255-48-2] + TX, cyproconazole [94361-06-5] + TX, difenoconazole [119446-68-3] + TX, diniconazole [83657-24-3] + TX, epoxiconazole [106325-08-0] + TX, fenbuconazole [114369-43-6] + IS TX, fluquinconazole [136426-54-5] + TX, flusilazole [85509-19-9] + TX, flutriafol [76674-21-0] + TX, hexaconazole [79983-71-4] + TX, imazalil [35554-44-0] + TX, imibenconazole [86598-92-7] + TX, ipconazole [125225-28-7] + TX, metconazole [125116-23-6] + TX, myclobutanil [88671-89-0] + TX, pefurazoate [101903-30-4] + TX, penconazole [66246-88-6] + TX, prothioconazole [178928-70-6] + TX, pyrifenox [88283- 41-4] + TX, prochloraz [67747-09-5] + TX, propiconazole [60207-90-i] + TX, simeconazole [149508-90-7] + TX, tebuconazole [107534-96-3] + TX, tetraconazole [1 1228L-77-3] + TX, triadimefon [41121-43-3] + TX, triadimenol [55219-65-3] + TX, triflumizole [99387-89-0] + TX, triticonazole [13 1983-72-7] + TX, ancymidol [12771-68- 5] + TX, fenarimol [60168-88-9] + TX, nuarimol [63284-71-9] + TX, bupirimate [41483-43-6] + TX, dimethirimol [5221-53-4] + TX, ethirimol [23947-60-6] + TX, dodemorph [ 593-77-7] + TX, fenpropidine [67306-00-7] + TX, fenpropimorph [67564- 91-4] + TX, spiroxamine [118134-30-8] + TX, tridemorph [81412-43-3] + TX, cyprodinil [12552-61-2] + TX, mepanipyrim [110235-47-7] + TX, pyrimethanil [53112- 28-0] + TX, fenpiclonil [74738-17-3] + TX, fludioxonil [13 1341-86-1] + TX, benalaxyl [71626-11-4] + TX, furaiaxyl [57646-30-7] + TX, metalaxyl [57837-19-1] + TX, R-metalaxyl [70630-17-0] + TX, ofurace [58810-48-3] + TX, oxadixyl [77732-09-3] + TX, benomyl [17804-35-2] + TX, carbendazim [10605-21-7] + TX, debacarb [62732-91- 6] + TX, fuberidazole [3878-19-1] + TX, thiabendazole [148-79-8] + TX, chlozolinate [84332-86-5] + TX, dichlozoline [24201-58-9] + TX, iprodione [36734-19-7] + TX, myclozoline [54864-61-8] + TX, procymidone [32809-16-81 + TX, vinclozoline [5047 1- 44-8] + TX, boscalid [188425-85-6] + TX, carboxin [5234-68-4] + TX, fenfuram [24691-80-31 + TX, flutolanil [66332-96-5] + TX, mepronil [558 14-41-0] + TX, oxycarboxin [5259-88-1] + TX, penthiopyrad [183675-82-31 + TX, thifluzamide [130000- 40-7] + TX, guazatine [108173-90-6] + TX, dodine [2439-10-31 [112-65-21 (free base) + TX, iminoctadine [13516-27-31 + TX, azoxystrobin [131860-33-8] + TX, dimoxystrobin [149961-52-41 + TX, enestroburin {Proc. BCPC, mt. Congr., Glasgow, 2003, 1, 93} + TX, fluoxastrobin [36 1377-29-9] + TX, kresoxim-methyl [143390-89-0] + TX, metomi- nostrobin [133408-50-1] + TX, trifloxystrobin [141517-21-7] + TX, orysastrobin [248593-to 16-0] + TX, picoxystrobin [117428-22-5] + TX, pyraclostrobin [175013-18-0] + TX, ferbam [14484-64-1] + TX, mancozeb [8018-01-7] + TX, maneb [12427-38-2] + TX, metiram [9006-42-2] + TX, propineb [12071-83-9] + TX, thiram [137-26-8] + TX, zineb [12122-67-7] + TX, ziram [137-30-4] + TX, captafol [2425-06-1] + TX, captan [133-06- 2] + TX, dichiofluanid [1085-98-9] + TX, fluoroimide [41205-21-4] + TX, folpet [133-is 07-3] + TX, tolylfluanid [731-27-1] + TX, bordeaux mixture [8011-63-0] + TX, copperhydroxid [20427-59-2] + TX, copperoxychlorid [1332-40-7] + TX, coppersulfat [7758-98-7] + TX, copperoxid [13 17-39-1] + TX, mancopper [53988-93-5] + TX, oxine-copper [10380-28-6] + TX, dinocap [13 1-72-6] + TX, nitrothal-isopropyl [0552-74-6] + TX, edifenphos [17109-49-8] + TX, iprobenphos [26087-47-8] + TX, isoprothiolane [50512-35-1] + TX, phosdiphen [36519-00-3] + TX, pyrazophos [13457-18-6] + TX, tolclofos-methyl [57018-04-9] + TX, acibenzolar-S-methyl [135158-54-2] + TX, anilazine [101-05-3] + TX, benthiavalicarb [41365-35-7] + TX, blasticidin-S [2079-00-7] + TX, chinomethionat [2439-01-2] + TX, chloroneb [2675-77-6] + TX, chiorothalonil [189 7-45- 61 + TX, cyflufenamid [180409-60-3J + TX, cymoxanil [5 7966-95-7] + TX, dichlone [/17-80-61 + TX, diclocymet [139920-32-4] + TX, diclomezine [62865-36-51 + TX, dicloran /99-30-91 + TX, diethofencarb [87/30-20-91 + TX, dimethomorph [110-188-70- 5] + TX, SYP-L190 ftlumorph) /211867-47-9J + TX, dithiation /3347-22-6] + TX, ethaboxam [162650-77-3J + TX, etridiazole [2593-15-91 + TX, famoxadone [/3/807-5 7- 3/ -TX fenamidone [161326-34-7/ + TX, fenoxanil [115852-48-7/ + TX, fentin [668- 34-8J + TX, ferimzone /89269-64-7] + TX, fluazinam /79622-59-6] + TX, fluopicolide [239110-15-7] + TX, flusulfamide [106917-52-6] + TX, fenhexamid [126833-17-8] + TX, fosetyl-aluminium [39148-24-8] + TX, hymexazol [10004-44-1] + TX, iprovalicarb [140923-17-7] + TX, IKF-916 (Cyazofamid) [120116-88-3J + TX, kasugamycin [6980- 18-3] + TX, methasulfocarb /66952-49-6/ + TX, metrafenone /220899-03-6/ + TX, pencycuron [66063-05-6] + TX, phthalide [27355-22-2] + TX, polyoxins [111 13-80-7] + TX, probenazole [27605-76-1] + TX, propamocarb [25606-41-1] + TX, proquinazid [189278-12-41+ TX, pyroquilon [57369-32-1] + TX, quinoxyfen [124495-18-71 + TX, quintozene [82-68-81 + TX, sulphur [7704-34-9] + TX, tiadinil [223580-51-6] + TX, triazoxide [72459-58-6] + TX, tricyclazole [418 14-78-2] + TX, triforine [26644-46-21 + TX, validamycin [37248-47-8] + TX, zoxamide (RH7281) [156052-68-51 + TX, mandipropamid [374726-62-2] + TX, isopyrazam [881685-58-1] + TX, sedaxane [874967- 67-6] + TX, 3 -difluoromethyl-1-methyl-i H-pyrazole-4-carboxylic acid (9-dichloromethylene-,2,3,4-tetrahydro-I,4-methano-naphthalen-5-yI)-amide (dislosed in WO to 2007/048556) + TX, 3-difluoromethyl-1-methyl-H-pyrazole-4-carboxylic acid [2-(2,4- dichlorophenyl)-2-methoxy-1 -methyl-ethyll-amide (disclosed in WO 2008/148570) + TX, 1- [4-[4-[(5S)5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1, 3-thiazol-2-yl]piperidin-1- yl]-2-[5 -methyl-3-(trifluoromethyl)-1H-pyrazol-1 -yljethanone + TX, 1 -[4-[4-[5-(2,6- difluorophenyl)-4,5-dihydro-1,2-oxazol-3-ylj-1,3-thiazol-2-yl] piperidin-1-yl]-2-[5-methyl-3-IS (trifluoromethyl)-I H-pyrazol-I -yI]ethanone [1003318-67-9], both disclosed in WO 2010/123791, WO 2008/013925, WO 2008/013622 and WO 2011/051243 page 20) +TX, 3-difluoromethyl-1 -methyl-i Fl-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yI)- amide (disclosed in WO 2006/087343) + TX, l-methyl-2-(2,4,5-trichloro-thiophen-3-yI)- ethyl] + TX, (S)-[3-(4-Chloro-2-fluoro-phenyl)-5 -(2,4-difluoro-phenyl)-isoxazol-4-y 11- pyridin-3-yl-methanol + TX, 3 -(4-Chloro-2-fluoro-phenyl)-5 -(2,4-difluoro-phenyl)- isoxazol-4-y l]-pyridin-3-yl-methanol + TX, (3-difluoromethyl--methyl-I H-pyrazole-4- carboxylic acid (3',4'-dichloro-5-fluoro-1, I -biphenyl-2-yI)-amide (bixafen) + TX, (N-{2- [3 -Chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl} -2-(trifluoromethyl)benzamid (fluopyram) + TX, N-[2-( I,3-dimethylbutyl)phenyl]-5-fluoro-I,3-dimethyl-I H-pyrazole-4-carboxamide (Penflufen) + TX, 1 -[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1 -piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-IH-pyrazol-I -yl]ethanone (CAS Reg.-No.: 1003318-67-9, oxathiapiprolin) + TX and 3-difluoromethyl-1 -methyl-IH-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yI)-amide (dislosed in WO 2006/087343) + TX, flupyradifurone (CAS registry number 951659-40-8) + TX, afidopyropen (CAS registry number 915972-17-7) + TX, pasteuria penetrans and TX, pasteuria spp. + TX, bacillus firmus +TX, bacillus cereus + TX, bacillus subtilis + TX and pasteuria penetrans +TX..

The references in brackets behind the active ingredients, e.g. [38 78-19-1J refer to the Chemical Abstracts Registry number. The above described mixing partners are known.

-120- Where the active ingredients are included in "The Pesticide Manual" [The Pesticide Manual -A World Compendium; Thirteenth Edition; Editor: C, D. S. TomLin; The British Crop Protection Council], they are described therein under the entiy number given in round brackets hereinabove for the particular compound; for example, the compound "abamectin" is described under entry number (1). Where "[CCNJ" is added hereinabove to the particular compound, the compound in question is included in the "Compendium of Pesticide Common Names", which is accessible on the internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; for example, the compound acetoprole is described under the internet address http://vvww.alanwood.net/pesticides/acetoprole.html. I0

Most of the active ingredients described above are referred to hereinabove by a so-called "common name", the relevant "ISO common name" or another "common name" being used in individual cases. If the designation is not a "common name", the nature of the designation used instead is given in round brackets for the particular compound; in that case, the ILJPAC IS name, the IUPAC/Chemical Abstracts name, a "chemical name", a "traditional name", a "compound name" or a "development code" is used or, if neither one of those designations nor a "common name" is used, an "alternative name" is employed. "CAS Reg. No" means the Chemical Abstracts Registry Number.

The active ingredient mixture of the compounds of formula I selected from table P with active ingredients described above comprises a compound selected from selected from Table I (compounds 1.1. to.75) or Table A (compounds Ito 7) and an active ingredient as described above preferably in a mixing ratio of from 100:1 to 1:6000, especially from 50:1 to 1:50, more especially in a ratio of from 20:1 to 1:20, even more especially from 10:1 to 1:10, very especially from 5:1 and 1:5, special preference being given to a ratio of from 2:1 to 1:2, and a ratio of from 4:1 to 2:1 being likewise preferred, above all in a ratio of 1:1, or 5:1, or 5:2,or5:3,or5:4,or4:1,or4:2,or4:3,or3:1,or3:2,or2:1,orl:5,or2:5,or3:5,or4: 5,or 1:4, or2:4, or3:4, or 1:3, or2:3, or 1:2, or 1:600, or L300, or 1:150, or 1:35, or2:35, or 4:35, or 1:75, or2:75, or4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or2:350, or4:350, or 1:750, or 2:750, or 4:750. Those mixing ratios are understood to include, on the one hand, ratios by weight and also, on the other hand, molar ratios, The mixtures as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to the pests or -121-their environment, with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.

The mixtures comprising a compound of formula I selected from selected from Table 1 (compounds 1.1. to 1.75) or Table A(compounds ito 7) and one or more active ingredients as described above can be applied, for example, in a single "ready-mix" form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a "tank-mix", and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, to such as a few hours or days. The order of applying the compounds of formula I selected from s&ected from Table 1 (compounds 1.1. to 1.75) or Table A (compounds ito 7) and the active ingredients as described above is not essential for working the present invention.

The compositions can also comprise further solid or liquid auxiliaries, such as stabilizers, for IS example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackitiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.

The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries). These processes for the preparation of the compositions and the use of the compounds! for the preparation of these compositions are also a subject of the invention.

The application methods for the compositions, that is the methods of controlling pests of the abovementioned type, such as spraying, atomizing, dusting, brushing on, dressing, scattering or pouring -which are to be selected to suit the intended aims of the prevailing circum-stances -and the use of the compositions for controlling pests of the abovementioned type are other subjects of the invention. Typical rates of concentration are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm, of active ingredient. The rate of application per -122-hectare is generally ito 2000 g of active ingredient per hectare, in particular 10 to 1000 g/ha, preferably 10 to 600 g/ha.

A preferred method of application in the field of crop protection is application to the foliage of the plants (foliar application), it being possible to select frequency and rate of application to match the danger of infestation with the pest in question. Alternatively, the active ingredi-ent can reach the plants via the root system (systemic action), by drenching the locus of the plants with a liquid composition or by incorporating the active ingredient in solid form into the locus of the plants, for example into the soil, for example in the form of granules (soil to application). In the case of paddy rice crops, such granules can be metered into the flooded

paddy-field.

The compositions according to the invention are also suitable for the protection of plant pro-pagation material, for example seeds, such as fruit, tubers or kernels, or nursery plants, IS against pests of the abovementioned type, The propagation material can be treated with the compositions prior to planting, for example seed can be treated prior to sowing. Alternative-ly, the compositions can be applied to seed kernels (coating), either by soaking the kernels in a liquid composition or by applying a layer of a solid composition. It is also possible to apply the compositions when the propagation material is planted to the site of application, for example into the seed furrow during drilling. These treatment methods for plant propagation material and the plant propagation material thus treated are further subjects of the invention, The compounds of formula (I) according to the invention can also be used in combination with safeners, Preferably, in these mixtures, the compound of the formula (I) is one of those specific compounds listed in Tables I (compounds 1.1. to 1.75) or a specific compound listed in Table A (compounds Ito 7), The following mixtures with safeners, especially, come into consideration: compound of formula (1) + cloquintocet-mexyl, compound of formula (I) + cloquintocet acid and salts thereol compound of formula (I) + fenchlorazole-ethyl, compound of formula (I) + fenchlorazole acid and salts thereof, compound of formula (I) + mefenpyr-diethyl, compound of formula (I) + mefenpyr diacid, compound of formula (I) + isoxadifen-ethyl, compound of formula (1) + isoxadifen acid, compound of fornmla (1) + furilazole, compound of formula (I) + furilazole R isomer, compound of formula (I) + benoxacor, compound of formula (I) + dichlormid, compound of formula (I) + AD-67, -123 -compound of formula (1) + oxabetrinil, compound of formula (1) + cyometrinil, compound of formula (1) + cyometrinil Z-isomer, compound of formula (1) + fenclorim, compound of formula (I) + cyprosulfamide, compound of fonriula (I) + naphthalic anhydride, compound of formula (I) + flurazole, compound of formula (I) + N-(2-methoxybenzoyl)-4- [(methylaminocarbonyl)aminojbenzenesulfonamide, compound of formula (I) + CL 304,415, compound of formula (I) + dicyclonon, compound of formula (I) + fluxofenim, compound of formula (I) + DKA-24, compound of formula (I) + R-29148 and compound of formula (I) + PPG-1292, A safening effect can also be observed for the mixtures compound of the formula (I) + dymron, compound of the formula (I) + MCPA, compound of the fonnula (I) + to mecoprop and compound of the formula (I) + mecoprop-P.

The mixing partners of the TX may also be in the form of esters or salts, as mentioned e.g. in The Pesticide Manual, 12th Edition (BCPC), 2000.

Is In the above different lists of active ingredients to be mixed with a TX, the compound of the formula I is preferably one specific compound listed in Table 1 (compounds 1.1. to 1.75) or one specific compound listed in Table A (compounds I to 7); and more preferably, a compound TX is selected from Table A and even more preferably a compound TX is selected from the compounds 1, 2, 3, 4, 5, 6, 7 of table A, or TX is selected from the compounds 1, 2, 4, 5, 6, 7 of table A. In the above-mentioned mixtures of compounds of formula I, in particular one specific compound listed in Table I (compounds 1.1. to 1.75) or one specific compound listed in Table A (compounds Ito 7), with other insecticides, fungicides, herbicides, safeners, adjuvants and the like, the mixing ratios can vary over a large range and are, preferably 100:1 to 1:6000, especially 50:1 to 1:50, more especially 20:1 to 1:20, even more especially 10:1 to 1:10. Those mixing ratios are understood to include, on the one hand, ratios by weight and also, on the other hand, molar ratios.

The mixtures can advantageously be used in the above-mentioned formulations (in which case active ingredient" relates to the respective mixture of TX with the mixing partner).

-124-Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type. In these circumstances other formulation types may be prepared. For example, where one active ingredient is a water insoluble solid and the other a water insoluble liquid, it may nevertheless be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the solid active ingredient as a suspension (using a preparation analogous to that of an SC) but dispersing the liquid active ingredient as an emulsion (using a preparation analogous to that of an EW). The resultant composition is a suspoemulsion (SE) formulation. I0

The mixtures comprising a TX selected from Table 1 (compounds 1.1. to 1.75) or Table A (compounds 1 to 7) and one or more active ingredients as described above can be applied, for example, in a single "ready-mix" form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a "tank-mix", IS and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. The order of applying the compounds of formula I selected from Table I (compounds 1,1, to 1.75) or selected from Table A (compounds I to 7) and the active ingredients as described above is not essential for working the present invention.

The compounds of formula (I) may be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.

Examples of suitable synergists for use in the compositions include piperonyl butoxide, sesamex, safroxan and dodecyl imidazole, Suitable herbicides and plant-growth regulators for inclusion in the compositions will depend upon the intended target and the effect required.

An example of a rice selective herbicide which may be included is propanil, An example of a plant growth regulator for use in cotton is PIXTM.

Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type. In these circumstances other formulation types may be prepared. For example, where one active ingredient is a water insoluble solid and the other a water insoluble liquid, it may nevertheless be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the solid active ingredient as a suspension -125 - (using a preparation analogous to that of an SC) but dispersing the liquid active ingredient as an emulsion (using a preparation analogous to that of anEW). The resultant composition is a suspoemulsion (SE) formulation.

In one embodiment the invention provides TX for use in controlling and/or preventing insects of the family Curcu//on/dae, preferably in for use in controlling and/or preventing Anthonoinus grand/s.

Additional examples of insects from the family of Curcu//on/dac are Anthonomus corvulus, Anthonoinus etutus, Anthonornus elongatus, Anthonornus eugen//, Anthonomus to consors, Anthonoinus haern a/opus, Anthonoinus Ieconte/, Anthonornus rnolochmus, Anthonomus inorlic/nus, Anthonornus musculus, Anthonornus nigrinus, Anthonornus phyf taco/a, Anthonornus p/c/us, Anthonoinus p0/forum, Anthonornus quadr/g/bbits', Anthonornus rect/rostris, Anihonornus rubE, Anthonornus santacruzi, Anthonornus s/gnat/is, Anthonornus sub,/àsciatus, and Anthonornus tenebrosus.

is In one embodiment the invention provides TX for use against Anthonornus grand/s in cotton.

In one embodiment the invention provides TX for use in controlling and/or preventing soil pests.

In one embodiment the invention provides TX for use in controlling and/or preventing corn rootworm, in particular for use against corn root worm from the genus Diahmtica.

In one embodiment the invention provides TX for use in controlling and/or preventing Diabrotica v/rgëra.

In one embodiment the invention provides TX for use in controlling and/or preventing Diabromica harheri.

In one embodiment the invention provides TX for use in controlling and/or preventing Diabrot/ca undecimpunctata howardi.

In one embodiment the invention provides TX for use in controlling and/or preventing wireworms, in particular Agriotes spp.

In one embodiment the invention provides TX for use in controlling and/or preventing Agriotes spp. in cereals, potato or corn, Additional examples of Agriotes spp. include Agriotes /ineatus, Agriotes obscurus, Agriotes brevis, Agriotes gurgistanus, Agriotes sputator, Agriotes ustulatus, Gte nicera destructo,;and LEmon/us ca/ifornicus.

-126-in one embodiment the invention provides TX for use in controlling and/or preventing grubs, in particular white grubs.

In one embodiment the invention provides TX for use in controlling and/or preventing Phyllophaga spp., particubrly on corn, soybean or cotton.

In one embodiment the invention provides TX for use in controlling and/or preventing Dilobodenis.spp. particularly on corn, soybean or cotton.

In one embodiment the invention provides TX for use in controlling and/or preventing Pop/li Ia japonica, particularly on corn, soybe2m or cotton.

Additional examples of white grubs include Phyliophagcs anxia, Phyl/ophaga to cr/nile, Phyl/ophaga suhniüda, Diiohoderu.s ahdentt In one embodiment the invention provides TX for use in controlling and/or preventing termites, e.g. on sugarcane.

Examples of termites include Reiicul!iertne.s; Copiolermes, Macroier,nes, Micmiernies; Globilermes, Specific of subterranean termites include Ref!cuiiferrnesflar!pes; IS Reticulitermes heperus, Reticitlitennes verginic its, Reticulitermes hageni, Ret/c zifitermes speratus, Reticuiltennes lucUligus, Heteroteruzes aureus, Coptotermes/brinosanus, Coptotermes acinacifhrmis, Coptotermes curvignathus, Nctsutiter;nes exitiosus, JVasutitermes iva/keri, Alastotermes darwiniensis, Schedorhinotennes spp, Iviacrotermes bel/icosus, Mucrotennes spp., Globitermes sulphureus Odontoterines spp.. Specific examples of dry wood termites include Juc/silermes minor, Margin/lermes hubbard!, Crypiotermes brevis, Ka/otermesfiavico/lis. Additional examples of termites include procormtermes spp. and procornilermes araujol In one embodiment the invention provides TX for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaplocoris pp. In one embodiment the invention provides TX for use in controlling and/or preventing Scaptocoris castaneus, in particular on cereals, soybean or corn.

In one embodiment the invention provides TX for use in controlling andlor preventing cutworms, e.g. agrotis spp..

In one embodiment the invention provides TX for use in controlling and/or preventing Agrolls ipsifori, particularly on cereals, canola, soybean or corn.

In one embodiment the invention provides TX for use in controlling and/or preventing millipedes, e.g. Jàlus spp..

In one embodiment the invention provides TX for use in controlling and/or preventing lulus spp., particularly on cereals, canola, soybean & corn.

-127-in one embodiment the invention provides TX for use in controlling and/or preventing broca gigante, e.g. Te/chin licits, particularly on sugarcane, In one embodiment the invention provides TX for use in controlling and/or preventing whitefly In one embodiment the invention provides TX for use in controlling and/or preventing Bern/s/a labaci, particularly on vegetables, cotton, soybean, or potatoes.

In one embodiment the invention provides TX for use in controlling and/or preventing Irta/eurodes vaporarion'rn, particularly on vegetables, cotton, soybean, or potatoes.

to In one embodiment the invention provides TX for use in controlling and/or preventing stinlcbugs, in particular lZuschi sins spp.

In one embodiment the invention provides TX for use in controlling and/or preventing Eu.s'ch/stus spp., particularly in soybeam Examples of stinkbugs include Nezara.spp. (e.g. Nezara v/nc/u/a, Nezara antennciIa, IS 7\Tezara hi/are), Piezodorus spp. (e.g. Piezodorus gui/din/i), A crosternurn spp. Euchistus spp.

(e.g. Euch/stus heros, Euschistus servus), Ha/yornoipha ha/ys, P/am/a crossola, Ritontus clavatus, 1?hopalus rnscuiatus, Antestiopsis orb/talus, Diche/ops spp. (e.g. Dichelops furcatus, Diche lops melacanthus), Eurygaster spp. (e.g. Eurygaster intengniceps, Eurygaster manna), Oeba/us spp. (e.g. Oebalus mnexicana, Oebaius poeci/us, Oe ba/us pugnase, Scot/nophara.spp. (e.g. Scol/nophara lun/da, Scol/nop/zara coarciata). Preferred targets include Antestiopsis orhitalus, Dicheiopsfiircatus, Dichelops rnelacanthus, Euchistus heros, Euschismus servus, l'/ezana v/n/c/u/a, 7\Tezara hi/are, Piezodorus gui/din/i, Ha/yornorpha halys.

In one embodiment the stinkbug target is Nezara vAr/c/u/a, Piezodorus spp., A crosternurn spp, Euchi sins henos, In one embodiment the invention provides TX for use against rice pests.

In one embodiment the invention provides TX for use against stemborer, particularly in rice.

Examples of stemborers include Chilo sp, Chulo siqpressalis, Chilopolychrysus, Chi/o ann/c/i/us, Scitpophaga spp., Scirpophaga incertu/as, Scitpophaga innotama, Scirpophaga n/pc//a Sesarn/a.sp, Sesarn/a /n/erens.

In one embodiment the invention provides TX for use against leaffolder, particularly in rice.

-128 -Examples of leaffolders include Cnaphalocroc/s spp., Cnaphaiocrocis med/nails; Zv[arasm/a spp., Alarasmia pa/nails, Itdarasmia exigna.

In one embodiment the invention provides TX for use against hoppers, particularly in rice.

Examples of Hoppers include Nephole/lix spp., Nepho/ellix v/re seem; Nephole liii nigropictus; Nephole/lix maiayanus, Nephote//ix cincliceps, N/iapar va/a ingens; Soga/elia Jurcifera.

In one embodiment the invention provides TX for use against galimidge, particularly in rice.

to Examples of Gall midge include Orseoi/a sp, Orseolia oryzae.

In one embodiment the invention provides TX for use against whorl maggot, particularly in rice.

Examples of whorl maggots include Hydrellia sp, Hydrelila ph/iepina.

in one embodiment the invention provides TX for use against Rice bugs, IS particularly in rice.

Examples of rice bugs indude Leptocorisa sp, Leptocor/sa orator/i s, Leptocor/sa chinensis, Leptocorisa acitta.

In one embodiment the invention provides TX for use against Black bugs, particularly in rice.

Examples of Black bugs include Scoliriophara.sp, Scolinophara coarciata, Scotinophara hir/da, Scotinophara latinscula.

In one embodiment the invention provides TX for use against phtteiia spp..

In one embodiment the invention provides TX for use against Pin/ella xyiostella, particularly in brassica crops.

in one embodiment the invention provides TX for use in controlling and/or preventing insects of the family (urcu/ionidae, preferably in for use in controlling and/or preventing Anthonomus grand/s.

Additional examples of insects from the family of Cwrcuiionidae are Anthonornus corvulus, Anthonoinus elutits, Anthonoinus elongatus, Anthonomus eugenli, Anthonoinus consors, Anihonomus haernatopus, Anihonomus iecorlei, An/honomus rnolochi ins, Anthonornus rnor/icinus; Anthonomus niu,scu Ins; Anthononnis n/grit/us; An/honomus phyllocoia, Anthonornus plc/us, A nthonomus porn orum, A nthonorn its quadrigibbus, Anthonom us rectirostris, Anthonomus rubi, Anthonomus santacruzi, Anthonomus s/gnu/us, Anthonomus sub/2isciatus, and Anthonoinus tenebrosus.

-129-in one embodiment the invention provides TX for use against Anihonornus grand/s in cotton.

In one embodiment the invention provides TX for use in controlling and/or preventing corn rootworm, in particular for use against corn root worm from the genus DEabrot/ca.

In one embodiment the invention provides TX for use in controlling and/or preventing corn Diabrot/ca virgifera.

to In one embodiment the invention provides TX for use in controlling and/or preventing corn D/abrofica barberi.

In one embodiment the invention provides TX for use in controlling and/or preventing corn 1)/abrot/ca undecimpunciala ho;1ardi.

In one embodiment the invention provides TX for use in controlling and/or IS preventing wireworms, in particular Agriotes Spp.

In one embodiment the invention provides TX for use in controlling and/or preventing Agriotes spp. in cereals, potato or corn.

Additional examples of Agriotes spp. include Agriotes 1/neatus, Agriotes obscurus, Agr/otes brev/s, Agriotes gut gisianus, Agr/otes sputator, Agr/otesustulaius, (ten/cera destructor,and L/inon/us cat ?forn/cus.

In one embodiment the invention provides TX for use in controlling and/or preventing grubs, in particular white grubs.

In one embodiment the invention provides TX for use in controlling and/or preventing Phyliophaga spp., particularly on corn, soybean or cotton.

In one embodiment the invention provides TX for use in controlling and/or preventing Dilohoderus spp. particularly on corn, soybean or cotton.

In one embodiment the invention provides TX for use in controlling and/or preventing Pop/il/a japonica, particularly on corn, soybean or cotton.

Additional examples of white gmbs include Phyilophaga a;jx/a, Phyilophaga cr/nile, Phyl/ophaga snbn/tida, D/ioboderus abdenis.

In one embodiment the invention provides TX for use in controlling and/or preventing tennites, e.g. on sugarcane, Examples of termites include 1?el/cu//tertnes, (optotermes, IWàcroter,nes, M/croternies, Glob/lermes, Specific of subterranean termites include Ret/cni/terrnesflai'/pes, -130-Reu/cui/ierrnes hesperus, ReIicuiiierrnes verginicus, Ret/cu/Hermes hageni, Reticulitermes speratus; Reticul/termes hicifligus, Heterolermes aureus, Coptolermes/brmosanus, (Joptotermes acinacijbrmis, (Joptotermes curvignathus, 7\/ctsutitermes cx; tiosus, ATasutiter;nes wa/ken, Mastotermes danwiniensis, Schedorhinotermes spp, Macrotermes beilicosus, Macrolermes spp., Glob/termes sit/phureus; Odontotermes spp.. Specific examples of dry wood termites include Incisilermes minor, Marginitermes hit bbardi, Crypiotermes brevis; Ka/oternzesflavico/iis. Additional examples of termites includeproconnitermes spp. and procornitermes araujol In one embodiment the invention provides TX for use in controlling and/or to preventing subterraneous stinkbugs, e.g. Scaptoconis spp.

In one embodiment the invention provides TX for use in controlling and/or preventing Scaptoconis castaneit, in particular on cereals, soybean or corn.

in one embodiment the invention provides TX for use in controlling and/or preventing cutworms, e.g. agro its spp.

is In one embodiment the invention provides TX for use in controlling and/or preventing Agrotis isiIon, particularly on cereals, canola, soybean or corn.

In one embodiment the invention provides TX for use in controlling and/or preventing millipedes, e.g. Julus spp., In one embodiment the invention provides TX for use in controlling and/or preventing lit/us spp., particularly on cereals, canola, soybean & corn.

In one embodiment the invention provides TX for use in controlling and/or preventing broca gigante, e.g. Teichin iicus; particularly on sugarcane, In one embodiment the invention provides TX for use in controlling and/or preventing whitefly, in one embodiment the invention provides TX for use in controlling and/or preventing Rem/sits tahaci, particularly on vegetables, cotton, soybean, or potatoes.

in one embodiment the invention provides TX for use in controlling and/or preventing Trialeurodes vaporaniorum, particularly on vegetables, cotton, soybean, or potatoes.

In one embodiment the invention provides TX for use in controlling and/or preventing stinkbugs, in particular.Eusch/siu,s' spp.

In one embodiment the invention provides TX for use in controlling and/or preventing Euschistus spp., particularly in soybean.

Examples of stinkbugs include Nezara spp. (e.g. Nezara viridula, Nezara antenna/a, Nezara hi lore), Piezodorus spp. (e.g. Piezodorus gui/din/i), Acrosfernuin spp. Euchis ins spp.

(e.g. Euchistus heros, Euschistus servus), Ha/yomorpha ha/ys, P/au/ia crossotci, Riptort us ciavatus, Rhopalus inscu/atus, Amestiopsis orbitalus, Diche/ops spp. (e.g. Dichelops irca/us, D/che/op,s' me/acanthus), Eurygaster.spp. (e.g. Euryga.ster infergriceps, Eurygaster rnaura), Oebaht.s.spp. (e.g. Oebahis inexicana, Oebaluspoec/lus, Oebaluspugnase, Scotinophara spp. (e.g. Scotinophara luridit, Scotinophara coarcicita). Preferred targets include An/c's/lops/s orbital us, Diche/ops flircafus, Dichelop.s nielacar thus, bichistus heros, Euschistus servus, //ezarci viric/u/a, Kezara hi/are, Piezodorus guild/nil, Halyornorpha halys.

to In one embodiment the stinkbug target is Nezara viridula, Piezodorus.spp., Acrosternuni.spp, Euchistus heros.

In one embodiment the invention provides TX for use against rice pests.

IS Examples of stemborers include (Jhiio sp, C/i/to suppressalis, Chi/opotychrysns, (h/to auriciiius, Scitpophaga spp., Scirpophaga incertulas, Scitpophaga innotaia, Scirpophaga u/vet/a Sesamia sp, Sesamia inferens.

Examples of leaffolders include Cnaphalocrocis spp., Cnaphalocrocis rnedinalis, Afarasnuce.spp., Marasmia pa/na/is, Afaras,nia exigua.

Examples of Hoppers include 7'Tephotettix spp., Nephotettir virescens, Nephotettix ungropictus, 7'Tephotettzr rna/ayanus, Nephote ft/i cincticeps, Ni/aparvata lugens, Sogatella furctera.

In one embodiment the invention provides TX for use against gallmidge, particularly in rice.

Examples of Gall midge include Orstolia.sp, Orseolia oryzae.

Examples of whorl maggots include Hydreilia p, Hydrelliaphitipina.

-132-in one embodiment the invention provides TX for use against Rice bugs, particularly in rice.

Examples of rice bugs include Leptocorisa sp, Leptocor/sa orator/its, Leptocorisa chuiensis, Leptocorisa acuta.

Examples of Black bugs include Scotinophara sp, Scot/nophara coarctata, Scotinophara fur/do, Scot/nophara fat/uscufa.

In one embodiment the invention provides TX for use against piutella spp..

to In one embodiment the invention provides TX for use against Piutella xylosteila, particularly in brassica crops.

The following Examples illustrate, but do not limit, the invention.

IS Preparation Examples

Examples

The following abbreviations were used throughout this section: s = singlet; bs = broad singlet; d = doublet; dd = double doublet; dt = double triplet; t = triplet, tt = triple triplet, q = quartet, sept = septet; m = multiplet; Me = methyl; Et = ethyl; Pr = propyl; Bu = butyl; Nip.

= melting point.

Example P1: N-[3-1[2,6-dibromo-4-1 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyllphenyl] carbamoyll-2-methoxy-phenyllthi etane-3 -carboxamide Step 1: N-[2,6-dibromo-4-[l,2,2,2-tetrafluoro-l -(trifiuoromethyl)ethyl]phenyl]-2-fluoro-N- (2-fluoro-3 -nitro-benzoyl)-3 -nitro-benzamide -133 - 23 g 2,6-dibromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline and 100 ml of tetrahydrofuran were placed in a 11 reactor under argon. 11.1 g of triethylamine, followed by 67 m8DN4AP, were added. Then 17.8 g 2-fluoro-3-nitro-benzoyl chloride was dissolved in ml of tetrahydrofbran and this solution was added dropwise to the reaction mixture, which was then stirred for 24 h at reflux, The mixture was allowed to cool to ambient temperature, poured into 400 ml of water and 400 ml of 2-methoxy-2-methyl-propane were added. The phases were separated and the organic phase was washed once with a saturated aqueous solution of sodium bicarbonate, The aqueous phases were combined and extracted three times with 2-methoxy-2-methyl-propane. The organic phases were combined, dried over to anhydrous sodium sulfate, filtrated and the solvent evaporated under vacuum, yielding 35,8 g of a dark brown solid. Purification by chromatography on silica gel, using dichloromethane!cyclohexane (5:5 to 8:2) as a solvent, yielded 26 g of N-[2,6-dibromo-4- [1,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl]-2-fluoro-N-(2-fluoro-3-nitro-benzoyl)- 3-nitro-benzamide as a white solid, M.p,: 220-222°C, is H NMR (CDCI3, 400 MHz): 8.13 ppm (m, broad, 2H), 8.02 ppm (m, broad, 2H), 7.86 ppm (s, broad, 2H), 7.37 ppm (m, broad, 2H).

Step 2: N-[2,6-dibromo-4-[1,2,2,2-tetrafluoro-1 -(trifluoromethvflethvl]phenyl]-2-methoxy-3-nitro-benzamide 26 g of N-[2,6-dibromo-4-[ 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-fluoro-N- (2-fluoro-3-nitro-benzoyl)-3-nitro-benzamide (Step 1) and 200 ml methanol were placed in a reactor, 23,8 g potassium carbonate was added, The mixture was stirred for 24 hat ambient temperature and then 24 h at 50°C. Then the mixture was poured slowly into 500 ml of water, then extracted with 500 ml of ethyl acetate. The aqueous phase was washed twice with 300 ml of ethyl acetate, The combined organic layers were dried over anhydrous sodium sulfate, filtrated and the solvent evaporated under vacuum, yielding a yellow solid, The residue was purified by chromatography on silica gel with ethyl acetate/cyclohexane (1:9 to 2:8). Thus, 19.9 g of N-[2,6-dibromo-4-[1,2,2,2-tetrafluoro-1 - (trifluoromethyl)ethyl]phenylj-2-methoxy-3-nitro-benzamide was obtained as a white solid, M.p.: 142-144°C.

-134-H NIVIR (CDC13, 400 MHz): 9.22 ppm (s, broad, 1H), 8.46 ppm (dd, 1H), 8.08 ppm (dd, IH), 7.90 ppm (s, 2H), 7,44 ppm (t, IH), 4.20 ppm (s, 3H).

Step 3: 3-amino-N-[2,6-dibromo-4-[1,2,2,2-tetrafluoro-1- (trifluoromethyflethyllphenyll-2-methoxy-benzamide F F BrO :* 2.00 g of N-[2,6-dibromo-4-[ 1,2,2,2-tetratluoro-1 -(trifluoromethyl)ethyl Iphenyl]-2-methoxy- 3-nitro-benzamide (Step 2) and S ml isopropanol were placed in a 100 ml flask under argon.

2.28 g of stannous chloride was added, followed by carefhl addition of 1.00 ml concentrated hydrochloric acid. The mixture was stirred for 1 hour at 90°C, then cooled to ambient temperature, concentrated under reduced pressure and the residue poured in water. Aqueous sodium hydroxide (2N) was added until the pH was in the range of 8 to 9. Then the aqueous phase was extracted twice with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtrated and the solvent evaporated under vacuum, yielding 1,91 g IS of a pale purple solid. The residue was purified by chromatography with ethyl acetate/cyclohexane (2:8) as a solvent. Thus, 1.60 g of 3-amino-N-[2,6-dibromo-4-[l,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyll-2-methoxy-benzamide was obtained as a white oily solid.

H NMR(CDCI3, 400 N'lflz): 9.55 ppm (s, broad, IH), 7.87 ppm (s, 2H), 7.58 ppm (dd, IH), 7.10 ppm(t, 1H), 6.98 ppm(dd, 1H), 4.01 ppm (s, 3H), 3.94 ppm (s, broad, 211).

Step 4: N-[3-[2,6-dibromo-4-[1,2,2,2-tetrafluoro-i -(trifluoromethyl)ethyl]phenyll carbamoyll-2-methoxy-phenyllthietane-3 -carboxamide F F BrO 68 mg thietane-3-carboxylic acid was dissolved in 4.8 mL of dry toluene and cooled to -10°, 81 p.1 triethylamine and 64mg ethyl chloroformate were added at -10°C. Then a solution of 328 mg 3-amino-N-[2,6-dibromo-4-[ 1,2,2,2-tetra±luoro-1 -(trifiuoromethyl)ethyl]phenyl]-2-methoxy-benzamide (Step 3) in 0.5 mL of dry toluene was added and the reaction mixture -135 -was stirred and allowed to reach ambient temperature. Then the mixture was heated to reflux for 5 mm and allowed to cool to ambient temperature. Mixture was diluted with dichloromethane, washed twice with NaOH (IN), then with brine, the organic layer was dried over anhydrous sodium sulfate and concentrated. The crude material was obtained as a brown oil, Purification by chromatography on silica gel, with heptane/ethyl acetate as a solvent, gave the product as a white solid, 330 mg. Further purification by preparative reversed phase chromatography yielded 80mg of N-[3-[2,6-dibromo-4-[1,2,2,2-tetrafluoro-I -(trifluoromethyl)ethyl]phenyljcarbamoylj-2-methoxy-phenyl]thietane-3 -carboxamide, H NMR (CDCI3, 400 MHz): 9.00 ppm (s, broad, IH), 8.50 ppm (d, IH), 7.91 ppm (s, broad, tO I H), 7.82 ppm (d, I H), 7.80 ppm (s 2H), 7.27 ppm (t, I H), 4.10 ppm (m, I H), 3.95 ppm (s, 3H), 3.60 ppm (t, 2H), 3.32 ppm (t, 2H).

Example P2: N-[3-1[2,6-dibromo-4-1 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyllphenyl] carbamoyll-2-methoxy-phenyll-I -oxo-thietane-3-carboxamide

F

71 mg ofN-[3-[2,6-dibromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl) ethyflphenyl] carbamoyl]-2-methoxy-phenyljthietane-3 -carboxamide (Example P1, Step 4) was dissolved in.0 ml dichloromethane, then II mg of 3-chlorobenzenecarboperoxoic acid was added and the reaction mixture was stirred at ambient temperature for 1.5 h. Then saturated aqueous sodium hydrogenocarbonate solution was added. The phases were separated, the organic layer was dried over anhydrous sodium sulfate and concentrated. Crude material was obtained as a beige solid, 68 mg. Purification by chromatography on silica gel, heptane/ethyl acetate (50:50 to 0:100) yielded 12.5 mg of N-[3-[2,6-dibromo-4-[1,2,2,2-tetrafluoro-I- (trifiuoromethyl)ethyljphenyl]carbamoyl]-2-methoxy-phenylj-I -oxo-thietane-3 -carboxamide.

1H NIN'IR (CDC15, 400 MHz): 8.96 ppm (s, broad, III), 8.55 (d, 1H), 7.90 ppm (m, 4H), 7.35 ppm(t, 1H), 4.02 ppm (s, 3H), 4.00 ppm (m, IH), 3.90 ppm (m, 2H), 3.44 ppm (m, 2H).

Example P3: N-[3-1[2,6-dibromo-4-[] ,2,2,2-tetrafluoro-I -(trifluoromethyl)ethyllphenyl] carbamoyll-2-methoxy-phenyll-1,1 -dioxo-thietane-3-carboxamide -136-

F

FF ri F Br

mg of N-[3-[2,6-dibromo-4-[ ,2,2,2-tetrafluoro--(trifluoromethyl)ethyflphenyl] carbamoyl]-2-methoxy-phenyllthietane-3 -carboxamide (Example P1, Step 4) was dissolved in 2.0 ml dichloromethane, then 42 mg of 3-chlorobenzenecarboperoxoic acid was added and the reaction mixture was stirred at ambient temperature for 1.5 h. Then saturated aqueous sodium hydrogenocarbonate solution was added. The phases were separated, the organic layer was dried over anhydrous sodium sulfate and concentrated, Crude material was obtained as an orange oil, 144 mg. Purification by chromatography on silica gel, heptane/ethyl acetate (30:70, then 50:50, then 0:100) yielded 34mg of N-[3-[2,6-dibromo- to 4-[ I,2,2,2-tetrafluoro--(trifluoromethyl)ethyl]phenyfl carbamoyl]-2-methoxy-pheny-1,1 -dioxo-thietane-3-carboxamide.

1H NIIvIR (CDGI3, 400 Yll-iz): 8.90 ppm (s, broad, in), 8.41 ppm (dd, in), 8.16 ppm (s, broad, iH), 7.83 ppm (dd, 1H), 7.80 ppm (s, 211), 7.25 ppm (t, IH), 4.52 ppm (m, 2H), 4.30 ppm (m, 211), 3.94 ppm (s, 311), 3.33 ppm (m, iH).

Example P4: N-[3-1[2,6-dibromo-4-1 1,2,2,2-tetrafiuoro-i-('trifluoromethyl)ethyllphenyl] carbamovll-2-methoxv-phenylldithiolane-4-carboxamide F F BrO 24mg dithiolane-4-carboxylic acid was dissolved in 3.0 ml dichloromethane and then cooled to 0°C. Then a drop of N,N-dimethylformamide and 20 mg oxalyl dichloride were added.

The mixture was allowed to reach ambient temperature. Then a solution of 90mg 3-amino- N-[2,6-dibromo-4-[ I,2,2,2-tetrafluoro-] -(trifluoromethyl)ethyl]phenyl]-2-methoxy-benzamide (Example Pi, Step 3) and of 16mg triethylamine in 2.0 ml dichloromethane was added and the reaction mixture was stirred at ambient temperature for i8 h. Then the mixture was concentrated to give a pale yellow solid, 266 mg. The residue was dissolved in dichloromethane, washed with water, dried over anhydrous sodium sulfate and concentrated.

The crude product was obtained as a brown solid, iSS mg. It was purified by chromatography on silica gel with heptane/ethyl acetate (30:70 to 50:50) as a solvent.

-137-Further purification by preparative reversed phase chromatography yielded the desired product in pure form. Thus, 8mg of N-[3-[2,6-dibromo-4-[l,2,2,2-tetrafluoro-1- (trifiuoromethyl)ethyl]phenyl] carbamoyl]-2-methoxy-pheny dithiol ane-4-carboxami de was obtained.

H Nvffl.(CDC13, 400 N'Mz): 9.10 ppm (s, broad, IH), 8.55 ppm (d, IH), 8.32 ppm (s, broad, IH), 7.90 ppm (d, 1H), 7.87 ppm (s, 2H), 7.33 ppm (t, IH), 4.01 ppm (s, 3H), 3.55 ppm (m, SB).

Example PS: N-[3-1[2,6-dibromo-4-11,2,2,2-tetrafluoro-I -(trifluoromethyl)ethyllphenyl] to carbamoyll-2-methoxy-phenylltetrahydrothiopyran-4-carboxamide F? F)A%1⁄4Br 0 S 530mg tetrahydrothiopyran-4-carboxylic acid was dissolved in 10.4 ml dichloromethane and a drop of DMF was added to the resulting solution. 484 mg oxalyl chloride was added dropwise to the solution and the mixture was stirred for 2 h at ambient temperature to yield a IS solution of tetrahydrothiopyran-4-carbonyl chloride, Then 1.978 of 3-amino-N-[2,6-dibromo-4-[ 1,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl]-2-methoxy-benzamide (Example P1, Step 3) and 687 mg pyridine were dissolved in 5.0 ml dichloromethane and the solution of tetrahydrothiopyran-4-carbonyl chloride was added dropwise. The mixture was stirred at ambient temperature for 4 h. Then the mixture was extracted with an aqueous potassium carbonate solution, the organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was suspended in methanol and stirred at 50°C for 30 mm, then the suspension was cooled to ambient temperature and filtered, The white filter cake was dried. Thus, 1.79 g of N-[3-[2,6-dibromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl] phenyl]carbamoyl]-2-methoxy-phenyljtetrahydrothiopyran-4-carboxamide was obtained as a 23 solid, M.p. > 220 CC, H NMR (DMSO-d(;, 400 Ml-lz): 10.48 ppm (s, broad, H), 9.50 ppm (s, broad, I H), 8.03 ppm(d, 1B), 8.01 ppm (s, 2H), 7.50 ppm (d, 1B), 7.23 ppm (t, 111), 3.85 ppm (s, 3H), 2.68 ppm (m, SH), 2.10 ppm (m, 2H), 1.75 ppm (m, 2H).

-138- Example P6: N-[3-1[2,6-dibromo-4-[1,2,2,2-tetrafluoro-1- (trifluoromethyl)ethyllphenyl] carbamoyll-2-methoxy-phenyll-I -oxo-thiane-4-carboxamide 0.80 g of N-[3-[2,6-dibromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyfl phenyl]carbamoyl]-2-methoxy-phenyl]tetrahydrothiopyran-4-carboxamide (Example P5) was dissolved in 115 ml dichloromethane and the resulting solution was cooled to 0°C in an ice bath, Then 0,27 g of 3-chlorobenzenecarboperoxoic acid was added and the solution was stined for 0 mm, The mixture was washed with a saturated aqueous solution of sodium bicarbonate and then with water. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by chromatography on silica gel, using dichloromethane!methanol (93:7) as a solvent. Thus, 735 mg of N-[3-[2,6-dibromo-4- [1,2,2,2-tetrafluoro-I -(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-methoxy-phenyl]-I -oxo-thianc-4-ca.rboxamidc was obtaincd as a mixture of two stcrcoisomcrs, white solid, M.p. = 151-152 CC.

H NMR (CDCI3, 400 MHz): 9.02 and 9.10 ppm (twos, IH total), 8.52 (m, IH), 7.80-7.90 ppm (m, 411), 7.32 ppm(t, in), 4.02 ppm (s, 3H), 3.33 ppm (m, in), 3.20 ppm (m, 111), 2.70 ppm (m, 111), 2.60 ppm (m, 4H), 2.10 ppm (m, 2H).

Example P7: N-[3-1[2.6-dibromo-4-[1,2,2,2-tetrafiuoro-1- (trifluoromethyflethyliphenyl] carbamoyll-2-methoxy-phenyll-1,1 -dioxo-thiane-4-carboxamide

F

mg N-[3-[2,6-dibromo-4-[i,2,2,2-tetrafluoro-1 -(trifiuoromethyl)ethyl] phenyl]carbamoyl]-2-methoxy-phenyljtetrahydrothiopyran-4-carboxamide (Example PS) was dissolved in 6 ml dichloromethane and afterwards 141 mg of 3-chlorobenzenecarbo-peroxoic acid was added. The resulting yellow solution was stirred for 18 hat ambient -139-temperature. Presence of PT-813 1(E) was monitored in LC/MS, The mixture was washed with aqueous sodium hydroxide solution (iN), then the organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by chromatography on silica gel, using dichloromethane/methanol (95:5) as a solvent. Thus, 161 mg of N-[3-[2,6- dibromo-4-[ 1,2,2,2-tetrafiuoro-1 -(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-methoxy-phenyl]-1, 1-dioxo-thiane-4-carboxamide was obtained as a white solid, M.p. = 152-155 °C.

H NIIvIR (CDGI3, 400 Yll-1z): 8.96 ppm (s, broad, in), 8.51 ppm (d, in), 7.91 ppm (d, in), 7.88 ppm (s, 2H), 7,77 ppm (s, broad, 1H), 7.34 ppm (t, 1H), 4.02 ppm (s, 3H), 3.42 ppm (m, 2H), 3.06 ppm (m, 2H), 2.69 ppm (m, I H), 2.50 ppm (m, 4H). I0

Example P8: N-[3-1[2,6-dibromo-4-1 1,2,2,2-tetrafluoro-1- (trifluoromethvl)ethvllphenvll carbamovll-2-methoxv-phenvll-I -(2,4-dioxotetrahvdroffiran- 3 -yliden&)thiane-4-carboxamide 150 mg of N-[3-[2,6-dibromo-4-[i,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylj phenyl]carbamoyl]-2-methoxy-phenyl Itetrahydrothi opyran-4-carboxami de (Example PS), mg (2,4-dioxotetrahydroftiran-3-id-3-yl)-phenyl-iodonium and S mg rhodium(1l) acetate were dissolved in 1 ml 1,2-dichloroethane. The mixture was heated to 60 °C and stirring was continued overnight. Then mixture was allowed to cool to ambient temperature and the solvent was evaporated under reduced pressure. The residue was purified by chromatorgraphy on silica gel, using ethyl acetate/methanol (9:1) as a solvent. Thus, 19 mg of N-[3 -[2,6-dibromo-4-[ I,2,2,2-tetrafluoro-1 -(trilluoromethyl)ethyl]phenyl]carbamoyl]-2-methoxy-phenylj-1 -(2,4-dioxotetrahydrofuran-3 -ylidene)thiane-4-carboxamide was obtained as a solid, M.p. = 188-192 °C.

H NIIVIR (CDC15, 400 MHz): 9.01 ppm (s, broad, In), 8.48 ppm (d, in), 8.03 ppm (s, broad, In), 7.90 ppm (d, IH), 7.86 ppm, (s, 2H), 7.33 ppm (t, IH), 4.45 ppm (s, 2H), 4.40 ppm (m, 21-I), 4.03 ppm (s, 3H), 3.20 ppm (m, 2H), 2.80 ppm (m, IH), 2.54 ppm (m, 2H), 2.25 ppm (m, 2H).

-140- Example P9: N-[3-1[2,6-dibromo-4-[1,2,2,2-tetrafluoro-1- (trifluoromethyl)ethyllphenyl] carbamoyll-2-methoxy-phenyll-1 -(dicyanomethylene)thiane 4-carboxamide FI I? HAQ% 150 mg of N-[3-[2,6-dibromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylj phenyl]carbamoyl]-2-methoxy-phenyl Itetrahydrothi opyran-4-carboxami de (Example PS) was dissolved in 2.2 ml diethyl ether and 31 mg oxirane-2,2,3,3-tetracarbonitrile was added at ambient temperature. Then the mixture was stirred for 3h, another portion of 31 mg oxirane-2,2,3,3-tetracarbonitrile was added, and the reaction was stirred for 18 hat ambient to temperature. Then the mixture was heated to 40°C for 18 h, then the solvent was evaporated and the residue was purified by chromatography on silica gel, using cyclohexane/ethyl acetate (30:70 to 0:100) as a solvent. Thus, 110mg of N-[3-[2,6-dibromo-4-[1,2,2,2- tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl]carbamoyl] -2-methoxy-phenyl]-1- (dicyanomethylene)thiane-4-carboxamide was obtained as a beige solid, M.p. = 167-173 °C.

1H NIN'IR (CDC13, 400 Yll-1z): 8.94 ppm (s, broad, 1H), 8.50 ppm (d, 1H), 7.88 ppm (m, 4H), 7.33 ppm (t, 1H), 4.03 ppm (s, 3H), 3.48 ppm (m, 2H), 3.35 ppm (m, 211), 2.57 ppm (m, 311), 2.35 ppm (m, 2H).

Example P 10: N-[3-1[2,6-dibromo-4-1 1,2,2.2-tetrafluoro-1- (trifluoromethyflethyliphenvl] carbamovll-2-methoxv-phenvll-I -imino-1 -oxo-thiane-4-carboxamide 400 mg of N-[3 -[2,6-dibromo-4-[ 1,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyllphenyl] carbamoyl]-2-methoxy-phenyl]-I -oxo-thiane-4-carboxamide (Example P6) was dissolved in dichloromethane and 90mg magnesium oxide, 127mg trifluoroacetamide, 271 mg diacetoxyiodobenzene and 7 mg rhodium(lI) acetate were added subsequently. The resulting suspension was stirred for 18 h at ambient temperature,Then the solvent was evaporated and -141-the residue taken up in 20 ml MeOl-1 and 387 mg potassium carbonate was added. This mixture was stirred for 3 h at ambient temperature. Then the solvent was evaporated and the residue purified by chromatography on silica gel, using dichloromethane/methanol (100:0 to 93:7) as a solvent. Thus, 124mg of N-[3-[2,6-dibromo-4-[1,2,2,2-tetrafluoro-1- (trifluoromethyl)ethyl]phenyl] carbamoyl]-2-methoxy-phenylj-I -imino-1 -oxo-thiane-4-carboxamide was obtained as a white solid, M.p. = 135-137 °C.

H INIIvIR (CDC13, 400 MHz): 9.00 ppm (s, broad, 1H), 8.50 ppm (d, 1H), 7.90 ppm (m, 4H), 7.33 ppm (t, IH), 4.04 ppm (s, 3H), 3.50 ppm (m, 2H), 3.32 ppm (m, 2H), 2.73 ppm (m, 2H), 2.50 ppm (m, 4H). I0

Example P11: 1-cvanoimino-N-13-[2,6-dibromo-4-[1,2,2,24etrafluoro-1- (trifluoromethvl)ethvllphenvll carbamovll-2-methoxv-phenvll-I -oxo-thiane-4-carboxamide FO12Xc! mg of N-[3 -[2,6-dibromo-4-[ 1,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyllphenyl] carbamoyl]-2-methoxy-phenyl]-I -imino-1 -oxo-thiane-4-carboxamide (Example P 10) was dissolved in 5.16 ml dichloromethane, then 22mg carbononitridic bromide and 15 mg N,N-dimethylpyridin-4-amine were added to the resulting solution. The solution was stirred at ambient temperature overnight. Then the solvent was evaporated and the residue puified by chromatography on silica gel, using dichloromethane/methanol (100:0 to 93:7) as a solvent.

Thus, 53 mg I-cyanoimino-N-[3-[2,6-dibromo-4-[1,2,2,2-tetra±luoro-I- (trifluoromethyl)ethyl]phenyl] carbamoyl]-2-methoxy-phenyll-I -oxo-thiane-4-carboxamide was obtained as a solid, M.p. = 170-174 °C.

H NMR (CDC13, 400 MHz): 8.92 ppm (s, broad, IH), 8.50 ppm (d, IH), 7,40 ppm (m, 4H), 7.35 ppm (t, 1H), 4.03 ppm (s, 3H), 3.94 ppm (m, 2H), 3.50 ppm (m, 2H), 2.83 ppm (m, 1H), 2.50 ppm (m, 4H).

Example P12: [4-[3-1[2.6-dibromo-4-11,2,2,2-tetrafluoro-1- (trifluoromethyflethyliphenyl] carbamoyll-2-methoxy-phenvllcarbamoyllthian-1-vlidenelammonium 2,4,6-trimethylbenzenesulfonate -142-FyJYcVO mg of N-[3 -[2,6-dibromo-4-[ 1,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyfl phenyl]carbamoyl]-2-methoxy-phenyl]tetrahydrothi opyran-4-carboxami de (Example PS) was suspended in imi of dichioromethane and 258 mg amino 2,4,6-trimethylbenzenesulfonate was added at ambient temperature. The white mixture changed directly to a solution and few minutes later to a white suspension again. The suspension was stined at ambient temperature for]h, The mixture was filtered and the filter cake was washed with 0.Sml of dichloromethane. The filter cake was dried in vacuo and the mother liquor was evaporated and dried in vacuo too. Thus, a combined yield of 142 mg [4-[3- [2,6-dibromo-4-[ 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl] -2-methoxy-phenyl]carbamoyl]thian-I -ylidenejammonium 2,4,6-trimethylbenzenesulfonate was obtained as a solid, M.p. >220 °C.

1H NIIvIR (DMSO-d6, 400 MT-Iz): 10.47 ppm (s, 1H), 9.68 ppm (s, IH), 8.07 ppm (d, 1H), 8.03 ppm(s, 2H), 7.51 ppm (d, IH), 7.24 ppm (t, IH), 6.74 ppm (s, 2H), 6.12 ppm (s, 211), IS 3.85 ppm (s, 3H), 3.70 ppm (m, 2H), 3.25 ppm (m, 2H), 2.90 ppm (m, lI-I), 2.40 ppm (m, 2H), 2.16 ppm (s, 3H), 2.03 ppm (m, 211).

Example P13: 1-cyanoimino-N-13-[2,6-dibromo-4-[1,2.2.2-tetrafluoro-1- (trifluoromethyl)ethyllphenyl] carbamoyll-2-methoxy-phenvll-] -imino-thi ane-4-carboxamide mg of [4-[3-[2,6-dibromo-4-[ ,2,2,2-tetrafluoro--(trifluoromethyl)ethyljphenyl] carbamoyl]-2-methoxy-phenyljcarbamoyl]thian-1 -ylidene]ammonium 2,4,6-trimethylbenzenesulfonate (Example P12) was dissolved in Iml of N,N-dimethylformamide and the solution was cooled to 0°C under argon. Then 5 mg sodium carbonate was added, followed by 18 mg N-chlorosuccinimide, The mixture was stirred at 0 °C for 20 mm and then 23 mg monosodium cyanamide was added, Stirring was continued over 3 days at ambient temperature. Then the mixture was diluted with water and dichloromethane, -143 -followed by extraction The aqueous layer was washed twice with dichloromethane and the combined organic phases were dried over anhydrous sodium sulfate and evaporated. The residue was purified by chromatography on silica gel, using cyclohexane/ethyl acetate (50:50 to 0:100) as a solvent Thus, 27mg of i-cyanoimino-N-[3-[2,6-dibromo-4-[i,2,2,2- tetrafluoro-I -(trifluoromethyl)ethyl]phenyljcarbamoyl] -2-methoxy-phenyl]-1 -imino-thiane- 4-carboxamide was obtained as a brown solid H INIIvIR (CDGI3, 400 MHz): 8.93 ppm (s, in), 8.50 ppm (d, 1H), 7 87 ppm (m, 5H), 7 33 ppm(t, in), 403 ppm (s, 3H), 3 80 ppm (m, 2H), 3 45 ppm (m, 2H), 2.81 ppm (m, 1H), 2.50 ppm (m, 4H) I0 The compounds in table A were prepared in the same or a similar way as described above

Table A

No STRUCTURE RT [M+H] [M-H] Method MP C (nun) (measure (measured) 1 197 667. 669 ZCQ12

I

N

S

N

S

2 164 683,685 ZCQ12 "N 687

T I

3 176 699. 701 ZCQ12 r & .7 &* " 4 117 699,701 ZCQ12

I

t4 C t' "kr A & !t. C. -144-No STRUCTURE RT [MI-I-I] [M-H] Method MP C (mill) (measured) (measured) -----214 626 --20008 2311

-N

J

6 2 iO 694 696, 20008

N

-1\

7 199 657 Z0008 160-

-N -\ Il.

-U'1]_ -.f' 3 1 96 728 726, Z0008 180--730 185

---

-L ck t1.i: 9 196 642 Z0008 173--183

N--

C

N -

N

LNflTtL\i I omerA 1 94 642 Z0008 237----242 -c N---.

Isomer B -145 -No STRUCTURE RT [MI-I-I] [M-H] Method MP C (mill) (measured) (measured) 11 -----193 712714 --20008 1701 -716 193 t S N. .\ -tc ? IsomeF A 12 190 712714 20008 222-716 240 Isomer B 13 113 651,653 SOD11 257-655 258 >= -< H-ks n \.X=..t S 14 180 667,669 20011 115-671 117 _\ 105 683,685, Z0012 136-687 138 Li r "p <

-I -

- -<N-

--

-146-No STRUCTURE RT [MI-I-I] [M-H] Method MP C (mill) (measured) (measured) 16 -----099 749751 ---ZCQ12 182-753 186 -s-' - 17 1 06 715, 717 20012 161-719 165

I

L-

A -

J I l.1 ii 18 117 695,697 ZCQ12 699 220 -\ ;->44 t. L--

SI

19 099 711,713 ZCQ12 151-715 152 L. N " \ \< -S -\_ % --I-.' - 100 793,795 ZCQ12 188-797 192 1j -S.

I

-\\.-P.) P.) P.) P.) P.) 2 01 a w N -to -l

C C,

-I

C / , 9 9 /

-/ Y--/j C' 4 ° // / I 1/ / 3_ f--,, Cl /p'c j 6' ,2 1<1 o --0 - 0: 0: 0 0: o: a a, a a, a -4-U -J--J -J--J:* -i--U 00': 0101)N: (.)N: ao (00 00 _-4 C, + --4 -4 --4 -4 a): U1 N: N: C N (0 01 0 a fl C, a

N N N N N

o o 0 0 0 a N N N N N a

NV

N:* -40: -4-U (0(0: 0101: -u 0 (0-1 ao 401 O1N -U 0 Na NJ 2 -1 0) 0 to -l

C 0.

-I

C

4 7 7 -/ -1 // / / 7=-/ ?9##/)(4 / / r -t'-d / 4 c -/ 9? / C 7 7: / -ii 1/ 7: 1: -0 0 CD: CD: CC 0) -0 01 (ii Co 0): 0)NJ:cp+ -4 -4 0) (3,: Ca: C (0 NJ a fl

C

CD a

N N N

0: 0: 0: N) NJ a a.: o,a: D: CON) H: 0 -149-LC-MS Methods: SODI 1: SQD Mass Spectrometer from Waters (Single quadrupole mass spectrometer) Instrument Parameter: Ionization method: Electrospray Polarity: positive and negative ions to Capillary: 3.00kV Cone: 30.00 V Extractor: 2.00 V Source Temperature: 150°C, Desolvation Temperature: 250°C IS Cone Gas Flow: 50 L/l-lr Desolvation Gas Flow: 650 L/Hr Mass range: 100 to 900 Da Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector.

Solvent degasser, binary pump, heated column compartment and diode-array detector.

Column: Phenomenex Gemini CiS, 3 rim, 30 x 2mm, Temp: 60°C DAD Wavelength range (nm): 20 to 500 Solvent Gradient: A = H20 +5% MeOH + 0,05 % HCOOH B= Acetonitril + 0.05 % I-ICOOH Time A% B% Flow (mi/mm) 0.00 100 0 0.850 3.40 0 100.0 0.850 4.10 0 100.0 0.850 4.20 100 0 0.850 4.60 00 0 0.850 -150-ZCO 12: ZQ Mass Spectrometer from Waters (Single quadrup&e mass spectrometer) Instrument Parameter: Ionization method: Electrospray Polarity: positive and negative ions Capillary: 3.00kV Cone: 30 V to Extractor: 2.00 V Source Temperature: 150°C, Desolvation Temperature: 350C Cone Gas Flow: 50 Lu-Jr Desolvation Gas Flow: 400 L/Hr is Mass range: 100 to 900 Da Acquity UPLC from Waters: Binary pump, heated column compartment and diode-aray detector.

Column: Waters UPLC HSS T3, 1.8 im, 30 x 2.] mm, Temp: 60 °C DAD Wavelength range (nm): 210 to 500 Solvent Gradient: A = H20 + 5% MeOI-l + 0.05 % HCOOH B Acetonitril + 0.05 % HCOOH Time A% B% Flow (mI/mm) 0.00 90 10 0.85 1,20 0 100.0 0.85 1.50 0 100.0 0.85 -151-ZDQO8: ZQ Mass Spectrometer from Waters (Single quadrupole mass spectrometer) Instrument Parameter: Ionization method: Electrospray Polarity: positive and negative ions Capillary: 3.00kV Cone: 30 V Extractor: 2.00 V Source Temperature: 150°C, Desolvation Temperature: 350C Cone Gas Flow: 50 L/Hr Desolvation Gas Flow: 400 L/Hr Mass range: 100 to 900 Da Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector.

Column: Waters UPLC HSS T3, 1.8 km. 30 x 2.1 mm, Temp: 60 °C DAD Wavelength range (nm): 20 to 500 Solvent Gradient: A = 1420+5% MeOH + 0,05 % HCOOH B= Acetonitril + 0.05 % HCOOH Time A% B% Flow (mI/mm) 0.00 90 10 0.85 2.70 0 100.0 0.85 3.00 0 100.0 0.85 -152-ZDQ11: ZQ Mass Spectrometer from Waters (Single quadrupole mass spectrometer) Instrument Parameter: Ionization method: Electrospray Polarity: positive and negative ions Capillary: 3.00kV Cone: 30 V Extractor: 2.00 V Source Temperature: 150°C, Desolvation Temperature: 350C Cone Gas Flow: 50 L/Hr Desolvation Gas Flow: 400 L/Hr Mass range: 100 to 900 Da Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector.

Column: Waters UPLC HSS T3, 1.8 km. 30 x 2.1 mm, Temp: 60 °C DAD Wavelength range (nm): 20 to 500 Solvent Gradient: A = H20 +5% MeOH + 0.05 % HCOOH B= Acetonitril + 0.05 % HCOOH Time A% B% Flow (mI/mm) 0.00 90 10 0.85 2.70 0 100.0 0.85 3.00 0 100.0 0.85 -153 -ZDQ 12: ZQ Mass Spectrometer from Waters (Single quadrupole mass spectrometer) Instrument Parameter: Ionization method: Electrospray Polarity: positive and negative ions Capillary: 3.00kV Cone: 30 V Extractor: 2.00 V Source Temperature: 150°C, Desolvation Temperature: 350C Cone Gas Flow: 50 L/Hr Desolvation Gas Flow: 400 L/Hr Mass range: 100 to 900 Da Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector.

Column: Waters UPLC HSS T3, 1.8 km. 30 x 2.1 mm, Temp: 60 °C DAD Wavelength range (nm): 20 to 500 Solvent Gradient: A = 1420+5% MeOH + 0,05 % HCOOH B= Acetonitril + 0.05 % HCOOH Time A% B% Flow (mI/mm) 0.00 90 10 0.85 2.70 0 100.0 0.85 3.00 0 100.0 0.85 -154-

Biological examples

These Examples illustrate the insecticidal and acaricidal properties of the compounds of formula (I). The tests were performed as follows: Svodoplera it/torah's (Egyptian cotton leafworm): Cotton leaf discs were placed on agar in a 24-well microtiter plate and sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs were infested with 5 LI larvae, The samples were checked for mortality, feeding behavior, and growth regulation 3 days after treatment (DAT).

to The following compound gave at least 80% control of Spodopiera li/torah's: I, 2, 3, 4, 6, 8, 12, 14, 15, 17, 18, 19, 20, 21,23,24, 25, 27, 28.

Hello/h/s virescenc (Tobacco budworm): Eggs (0-24 h old) were placed in 24-well microtiter plate on artificial diet and treated with IS test solutions at an application rate of 200 ppm (concentration in well 18 ppm) by pipetting, After an incubation period of 4 days, samples were checked for egg mortality, larval mortality, and growth regulation, The following compound gave at least 80?/' control of ifeilothis virescens: I, 2 3 4 12 13, 14, 15, 17, 18, 19, 20, 21, 22,23,24, 25, 27, 28.

Phi/ella rylactelia (Diamond back moth): 24-well microtiter plate (rvlTP) with artificial diet was treated with test solutions at an application rate of 200 ppm (concentration in well 18 ppm) by pipetting. After drying, the MTP's were infested with L2 larvae (7-12 per well). After an incubation period of 6 days, samples were checked for larval mortality and growth regulation.

The following compound gave at least 80% control of P/u/ella xyloste//a: I, 2, 3 4, 5, 6, 8,9, 10, 11, 12, 14, 15, 16, 17, 19,21,22,23,24,27, Diabrotica balteata (Corn root worm): A 24-well microtiter plate (MTP) with artificial diet was treated with test solutions at a application rate of 200 ppm (concentration in well 18 ppm) by pipetting, After drying, the MTP's were infested with L2 larvae (6-10 per well). After an incubation period of 5 days, samples were checked for larval mortality and growth regulation.

-155 -The following compound gave at least 80% control of Diabrolica ballets/a: 1, 2, 3, 6, 15 17, 18,21,22,24,26,27.

Thns tabaci (Onion thrips): Sunflower leaf discs were placed on agar in a 24-well microtiter plate and sprayed with test solutions at an application rate of 200 ppm, After drying, the leaf discs were infested with all aphid population of mixed ages. After an incubation period of 7 days, samples were checked for mortality.

The following compounds gave at least 80% control of Thrijs lcthaci: I, 2, 3, 4, 5, 6, 8 to II, 12, 13, N, 5, 16, 17, 18, 19,20,21,22,23,24,26,27,28.

iètranj1'ciius urticae (Two-spotted spider mite): Bean leaf discs on agar in 24-well microtiter plates were sprayed with test solutions at an application rate of 200 ppm, After drying, the leaf discs are infested with mite populations of is mixed ages. 8 days later, discs are checked for egg mortality, larval mortality, and adult mortality.

The following compounds gave at least 80% control of iètranychus urticae: I, 2, 3, 4, 5 6,7,8,9, 10, II, 12, 13, 14, 15, 6, 17, 18, 19,20,21,23,24,26,27,28, Myzus persicae (Green peach aphid): Sunflower leaf discs were placed on agar in a 24-well microtiter plate and sprayed with test solutions at an application rate of 200 ppm, After drying, the leaf discs were infested with an aphid population of mixed ages. After an incubation period of 6 DAT, samples were checked for mortality, The following compounds gave at least 80% control ofA'zuspersicae: I, 2, 3, 6, 12, 13 14, 15, 16, 17, 8, 9,20,2I,22,23,25,26,27, Aedes aegypti (Yellow fever mosquito): Test solutions, at an application rate of 200ppm in ethanol, were applied to 12 well tissue culture plates, Once the deposits were dry, five, two to five day old adult female Aedes aegypli were added to each well, and sustained with a 10% sucrose solution in a cotton wool plug. Assessment of knockdown was made one hour after introduction, and mortality was

assessed at 24 and 48 hours after introduction.

-156-None of the prepared examples described in the table showed knockdown activity after one hour. The following compounds gave at least 80% control of Aedes aegypli after 48h and/or 24h: 6, 14, 15, 18, 19.

Anophe/es slephensi (Indian malaria mosquito): Test solutions, at an application rate of 200 ppm in ethanol, were applied to 12 well tissue culture plates. Once the deposits were dry, five, two to five day old adult female Anopheles siephensi were added to each well, and sustained with a 10% sucrose solution in a cotton wool plug. Assessment of knockdown was made one hour after introduction, and mortality to was assessed at 24 and 48 hours after introduction.

None of the prepared examples described in the table showed knockdown activity after one hour. The following compounds gave at least 80% control of Anophefes stephensi after 48h and/or24h: 6,15,18.

__________________________________

Claims

-157-

A compound of formula (I)

R (I) awherein Q' is a saturated 4-to 6-membered heterocyclic ring comprising one or two sulfur atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from =0, N-Z or CZ'Z2; Z is hydrogen or cyano Z is cyano Z2 is cyano or Z1 and Z2, taken together, form a bridge -C(O)-O-CH2-C(O)-or -C(O)-S-CH2-C(O)-Q2 is a moiety of formula (II) Yl (II)

-wherein Y' is selected from Cl, Br, 1, Ci4alkyl, Ci4alkoxy, Ci4haloalkyl, Ci4haloalkoxy, C1 4alkylthio, C1 4alkylsulfinyl, C i4alkylsulfonyl or Cialkoxy-i 4alkyl Y5 is selected from Cl, Br, I, Ci4alkyl, Ci4alkoxy, Ci4haloalkyl, Ci4haloalkoxy, C1 4alkylthio, C1 4alkylsulfinyl, C i4alkylsulfonyl or Ci4alkoxy-C1 4alkyl Y is Ci4haloalkyl xa is hydrogen, methoxy or halogen XL is hydrogen, halogen or cyano -158-R' is selected from hydrogen, Ci-Cgalkyl, C2-C8alkenyl, C2-Cgalkynyl, Ci-Cgalkylcarbonyl, Ci-C3alkoxycarbonyl, hydroxyl, C i-C3alkyloxy, and aminocarbonyl-Ci-C4alkylene; 1(
2 is selected from hydrogen, Ci-Cgalkyl, C2-Csalkenyl, C2-C8alkynyl, Ci-C8alkylcarbonyl, C i-Csalkoxycarbonyl, hydroxyl, C i-Csalkyloxy, and aminocarbonyl-C i-C4alkylene; and G' and G2 are both oxygen; or an agrochemically acceptable salt thereof 2. A compound of formula (I) according to claim 1 characterized in that R is selected from hydrogen, Ci-Cgalkyl, C2-Cgalkenyl; W is selected from hydrogen, Ci-Cgalkyl, C2-Cgalkenyl;
3. A compound of formula (I) according to claim 1 or claim 2 characterized in that Y' is selected from Cl, Br, I, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, trif'luoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl or IS methoxymethyl and Y5 is selected from Cl, Br, I, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, trifluoromethyl sulfinyl, trifluoromethyl sulfonyl or methoxymethyl
4. A compound of formula (I) according to claim 1 characterized in that xa is hydrogen, methoxy or F Xb is hydrogen, or cyano
5. A compound of formula (1) according to claim 4 characterized in that Y' is selected from Cl, Br, methyl, ethyl; and Y' is selected from Cl, Br, ethyl;
6. A compound of fonnula (V) -159-

R NQ xçwherein R is selected from OF-I, C-C6alkoxy, F, Cl or Br; Q1 is a saturated 4-to 6-membered heterocyclic ring comprising one or two suiftir atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from 0, N-Z or CZ1Z2; Z is hydrogen or cyano; Z' is cyano Z2 is cyano or Z1 and Z2, taken together, form a bridge -CO)-O-CH2-C(O)-or -C(0)-S-CH2-C(O)-; and the values of Xa, Xb and R' as set out above for the different embodiments of the present invention, or a salt thereof is
7. A process for the production of compounds according to the formula (1) or an agrochemicafly acceptable salt thereof characterized in that a compound according to the formula (V)

R NAQI xçwherein R is selected from OF-I, CI-C(;alkoxy, Cl, F or Br and the values of X', X" and R1 as set out above for the different embodiments of the present invention and Q' is a saturated 4-to 6-membered heterocyclic ring comprising one or two -160-sulfur atoms in addition to the carbon atoms, which may be unsubstituted or substituted on a sulfur atom with one or two substituents selected from =0, =N-Z or =CZ1Z2; Z is hydrogen or cyano Z1 is cyano Z2 is cyano or Z' and Z2, taken together, form a bridge -C(0)-0-CH2-C(0)-or -C(0)-S-CH2-C(0)-is reacted with and with an amine of formula NHR2Q2 wherein Q2 is a moiety of formula (II) Yl (II) y5y3 I0 and Y3 is heptafluoroprop-2-yl or nonafluorobut-2-yl 1(2, Y' and Y5 are, in any combination, as set out above for the different embodiments of the present invention.
8. A method of use of compounds according to the formula (IV) OMe xxa (IV) N,1 for the production of compounds according to formula (V) R NXQ1 wherein X and 1(1 have the meaning as set out above for the different embodiments of the present invention and preferably R1 is selected from methyl, ethyl, n-propyl and n-butyl, -161-R is selected from OH, Ci-C6alkoxy, Cl, F or Br and Q' is a saturated 4-to 6-membered heterocyclic ring containing one or two sulfur atoms or a salt thereof
9. A method of controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 6.to
10. An insecticidal, acaricidal, nematicidal or molluscicidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 6 together with an agrochemically acceptable diluent or carrier, is
II. A composition according to claim I which further comprises one or more additional insecticidal, acaricidal, nematicidal or molluscicidal compounds.
12. A method of protecting useful plants from insects, acarines, nematodes or molluscs, comprising applying to said plants, to the locus thereof, or to plant propagation material thereot an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula I in any one of claims i too